References

References "ortho and para bromophenyl isopropyl methylamines"

Serial number: 547,446 filed May 4 th, 1966 to Zoltan Ecsery, Jozsef Knoll , lidiko Kosa,
lidiko Sandor, Eva Somfai, and Sandor Totok, all of Budapest Hungary. Assigned to :
Chinoin Gyogyszer es Vegyeszeti Termekek Byara RT.
Serial number 437,012 , June 15", 1954 to Yvon J. L'italien, of Hazel Park Mi , and Mildred
C. Rebstock, of Detroit M i, assigned by Parke, Davis & Company.
"Tertiary butyl amines and their preparation"
Serial number 775 ,754 September 23 rd , 1947 by Liese L. Abell , of New york City, William
F. Bruce, of Havertwon, Pa, and Joseph Seifter, of Willow Grove, Pa., to Wyeth
Incorpora ted.
"Preparation of arylal iphatic amines"
th
Serial number 609,028, August 4 , 1945 by Chester M. Suter, of Albany N.Y., and Arthur
W. Weston, of Waukegan III. , assigned by Sharp & Dohme, Inc.
"beta-ortho-methoxyphenylpropyl methylamines"
Serial number: 386,661, April 3 rd , 1941 by Eugene H. Woodruff, from Kalamazo, Mich. , to
The UpJohn Company.
"Amino compound"
Serial number: 275,638, May 25 th , 1939 by Eugene H. Woodruff, from Kalamazo, Mich. ,
to The UpJohn Company.
"Stimulants suitable for combating symptoms of fatigue and process for their production"
Serial number 255 ,882, February II th , 1939 by Felix Haffner, and Fritz Sommer, both of
Berlin Germany--, to Allen property custodian
" Process of synthetically producing ephedrine homologue and its salts"
Serial number 433 ,816, March 6 th , 1930 to Chogi Nagai of Shibuya Machi Japan, by
Alexander NagaI, of Berlin Germany .
"Mydriatic and process of making same"
Serial number, 88,224, April 1st , 1916 by Wilhelm Nagajoshi , of Tokyo Japan, to M. Dick
Bunnell, of San Francisco, CA; also see Serial number, 433 ,816, March 6 th , 1930, by Chogi
Nagai of Tokyo, Japan, to Alexander Nagai, of Berlin Germany.

Titeler, M.; Lyon, R. A. ; Glennon, R. A. Psychopharmacol. 1988,94, 213 .

Wang, S, S.-H. ; Mathis, C. A.; Peroutka, S. 1 Psychopharmacol. 1988, 94, 431.
Ketones to amines
A.1. Vogel , Textbook of Practical Organic Ch emistry. 4th ed. (Longman Scientific and
Technical) New York, 1987. pp. 568-569.
A.C. Allen and W.O. Kiser, Methamphetamine from ephedrine: I. Chloroephedrine and
aziridines. J. Forensic Sci., 32 (1987) 953-962.
C.B. Lebrilla and W.F. Maier, C-H Activation on platinum, a mechanistic study. J. Am.
Chern. Soc .. 108 (1986) 1606-1616.
W.F. Maier, SJ . Chettle, R.S. Rai and G. Thomas, Metamorphosis of palladium and its
relation to selectivity in the Rosenmund reaction . J. Am. Ch ern. Soc .. 108 (1986) 2608-
2616.
F.T. Noggle, Jr., 1 DeRuiter and C.R. Clark, Liquid chromatogaphic determination of the
enantiomeric composition of methamphetamine prepared from ephedrine and
pseudoephedrine. Anal. Chern .. 58 (1986) 1643-1648.
Sharts, C. M. ; Shepard, W. A. Org. React. 1974, 21,125.
Cox, D. P.; Terpinski , 1 ; Lawrynowicz, W. 1 Org. Chern. 1984, 49, 32
Shulgin, A. T . in Handbook of Experimental Pharmacology, Vol. 55, Part II , Psychotropic
Agents; Hoffmeister, F.; Stille, G, Eds. ; Springer-Verlag: New York , 1982, pp 3-29.
Biomedical Aspects of Fluorine Chemistry; Filler, R,; Kobayashi , Y. Eds.; Kodansha Ltd.:
Tokyo, 1982.
Jackiela, D. 1; Helquist, P.; Jones, L. D. Org. Syn. 1984, 62 , 74
Djuric, S.; Venit, 1; Magnus, P. Tetrahedron Lett. 1981 , 22, 1787.
For a review ofheteroatom-facilitated lithiation reactions see, Gschwend, H. W.;
Rodriguez, H. R. Org. React. 1979, 26, I.
Quick, 1 ; Meltz, C. J. Org. Chern. 1979, 44, 573,
d-Phenylalanine carbamate reductions
R.B. Repke, D.K. Bates and WJ. Ferguson, Synthesis of dextroamphetamine sulfate and
253
 References
methamphetamine hydrochloride from d-phenylalanine.j. Pharm. Sci. , 67 (1978) 1168-
1169. C.A. 89: 163164h (1078).
F.A. Carey and RJ. Sundberg, Advanced Organic Chemistry, Part B. Plenum Press, New
York, N.Y., 1977.
Protection of amines followed by ether cleavage, Jung, M. E.; Lyster, M. A. J. Org. Chern.
1977, 42, 3761.
Shulgin, A. T. ; Dyer, D. C. J. Med. Chern. 1975, 18, 1201.
Schiff base reductions
8.H.G. Wassink, A. Duijndam and A.C.A. Jansen, A synthesis of amphetamine. 1. Chem.
Ed. , 51 (1974) 671. No C.A. citation.
Nichols, D. E.; Barfknecht, C. F.; Rusterholz, D. B. J. Med. Chern. 1973, 16, 482.
H.O. House, Modern Synthetic Reductions, second ed. Benjamin/Cummings Publiching
Co. , Phillippines, 1972.
Ketone reductions
R.F. Borch, M.D. Bernstein and H.D. Durst
The Cyanohydridiborate anion as a selective reducing agent. 1. Am. Chem. Soc., 93 (1971)
2897-2904. C.A. 75: 49525n (1971).
Shulgin, A. T.; Sargent, T.; Naranjo, C. Pharmacol. 1971 , 5, 1031
Barfknecht, C. F.; Nichols, D. E. J. Med. Chern. 1971 , 14,370.
E.H. Sund and H.R. Henze, Alkyl benzyl ketones and hydantoin derivatives. 1. Am. Chem.
Eng. Data. 15 (1970) 200.
A. McKillop and J.D. Hunt, Thallium in organic synthesis. XX. Oxidative rearrangement
of olefins with thallium (III) nitrate: A simple one-step synthesis of aldehydes and ketones.
Tetrahed. Lett., 60 (1970) 5275 .
Demercuration
H.C. Brown and J.T. Kurek, Solvomercuration-demercuration of representative olifins in
the presence of acetonitrile. Convenient procedure for the synthesis of amines. 1. Am.
Chem. Soc., 91(1969) 5647-5649. C.A. 71: 10126Ig(1969).
N-formylamphetamine reductions
O. Cervinka, E. Kroupova and O. Belovsky, Assymetric reactions. XXIX. Absolute
configuration ofphenyl-2-alkylamines and their N-methyl derivatives. Call. Czech. Chem.
Commun., 33(11) (1968) 3551-3557. C.A. 70: 37323d (1969).
Oxime reductions
K. Kotera, T. Okada and S. Miyazaki, Stereochemistry of aziridine formation by reduction
of oximes with lithium aluminum hydride on arylalkyl alkyl ketoximes and their tosylates.
Tetrahedron, 24 (1968) 5677-5690. C.A. 69: 67158a (1968).
Hydride reduction of related nitropropenes, Yoon, N. M. ; Brown, H. C. J. Am. Chern. Soc.
1968, 90,2927.
Ephedrine esters reduction
A. Larizza, G. Brancaccio and A. Segre, 1-, d- and d,I-Ephedrine phosphates. 1. Med.
Chem., 9 (1966) 996-997. C.A. 66: 28945y (1967).
Leuckart mechanisms
A. Lukasiewicz, The mechanism of the Leuckart-Wallach reaction and of the reduction of
Schiffbases by formic acid. Tetrah edron, 19 (1963) 1789-1799. C.A. 60: 1549f(1964).
Wagner, H. N.; Bums, H. D.; Dannal s, R. F.; Wong, D. F.; Langstrom, B.; Dueller, T.;
Frost, J. J.; Raven, H. E.; Links, J. M.; Rosenbloom, S. 8. ; Lukas, S. E.; Kramer, A. V.;
Kuhar, H. J. Science, 1983,22 1, 1264.
2-keto oxime reductions
P.L. Cook, The reduction of aldehydes and ketones with nickel-aluminum alloy in aqueous
alkaline solution. 1. Am. Chern. Soc., 27 (1962) 3873-3875 . C.A. 58: 464c (1963).
Schiff base reductions
J. Weichet, J. Hodrova and L. Blaha, reductive ami nation ofphenylacetylcarbinols by
sodium borohydride. Call. Czech. Chem. Commun., 26 (1961) 2040-2044. C.A. 56: 5864c
(1962).
Oxime reductions
T. Kametani and Y. Nomura, reduction of nitrogen compounds by Raney nickel alloy and
alkalai solution. I. 1. Parm. Soc. Jpn., 74 (1954) 413-416. C.A. 49 : 5342d (1955).
2-keto oxime reductions
W.H. Hartung and Y. Chang, Palladium catalysis. IV. Change in behavior of palladium-
254
 References
charcoal in hydrogenation reactions. J. Am. Chern . Soc., 74 (1952) 5927-5929. CA. 48:
115g(1954).
N itrostyrene reductions
R.T . Gilsdorfand F.F. Nord, Reverse addition of lithium aluminum hydride to nitroolefins.
J. Am. Chern. Soc., 74 (1952) 1837- 1843. CA. 48: 553c (1954).
Schiff base reductions
M. Tsutsumi, An illegal preparation of an amphetamine-like compound. Science Crime
Detect. , (Japan) 6 (1953) 50-52. CA. 47: 11661h (1953).
N itrostyrene reductions
G. Stochdorph and O . Schickh, Saturated amines. German Patent No . 848, 197, Sept. I,
1952. CA. 47: 5438b (1953).
Phenylacetic acid
M. Tsutsumi, An illegal preparation of an amphetamine-like compound. Science Crim e
Detect. (Japan), 6 (1953) 50-52. CA. 47 : 11661h (1953).
J.A. King and F.H. McMillan, The decarboxylative acylation of arylacetic acids. J. Am.
Chern. Soc. , 73 (1951) 4911-1915. CA. 47: 535a (1953).
Chloro ephedrine reduction
A. Gero, Some reactions of l-phenyl-l-chloro-2-methylaminopropane. I. Reaction with
metal s and hydrogen . J. Org. Chern., 16 (1951) 1731-1 735 . CA. 46: 6606g (1952).
2-Keto oxime reductions
V. Evdokimoff, Reduction reaction with nickel-aluminum alloy. Applications to the
synthesis of norephedrine and other pharmacologicall y active amines. Gazz. Chirn . Ita!. , 8 1
( 1951) 725-734. CA. 46: 7070d (1952).
Chloroephedrine reductions
A. Gero, Some reactions of l-phenyl-l-chloro-2-(methylamino)propane I. Reaction with
metal s and with hydrogen. J. Org, Ch ern., 16 (1951) 1731-1736. CA. 46: 6606g (1952).
Chloroephedrine reductions
A. Gero, Some reactions of l-phenyl-l-chloro-2-(methylamino )-propane. I. Reactions with
metal s and with hydrogen . J. Org. Chern., 16 (1951) 1731-1735. CA. 46: 6606g (1952).
Schiff base reductions
P. Mastigle, M. Metayer and A. Bricard, Study of the aminolys is of some ketones and
aldehydes. Bull. Soc. Chirn. France (1950) 1045- \048. CA. 45: 8970h (1951).
Oxime reductions
lW. Wilson, Synthesis of dl-amphetamine sulfate labeled with C 14 . J. Am. Pharrn. Assoc.,
(Sci. Ed.) , 39 (1950) 687. CA. 45 : 1728d (1951).
Hydrazone reductions
R. Fusco and L. Canonica, Reduction ofphenylhydrazone-p-sulfonic ac ids. Chirn Ind.
(Milan), 32 (1950) 208-210. CA. 45: 4645a (1951).
l W. wilson, Synthesis of dl-amphetamine sulfate labeled with C 14. J. Am. Pharrn. Assoc.,
(Sc i. Ed.), 39 (1950) 687. CA. 45 : 1728d (1951).
Conditions for organometallic opening of ethylene oxide followed from Gaylord, N. G. ;
Becker, E. T . Chern. Re v. 1951 , 49 , 413 .
Oxime reductions
H.B. Hass, A.G. Susie and B.L. Heider, Nitroalkane deri vat ives. J. Org. Chern. , 15 (1949)
8-14. C.A. 44: 4412d (1950).
N itrostyrene reductions
H.B . Hass, A.G. Susie and R.L. Heider, Nitro-alkane deri vatives. J. Org. Chern., 15 (1950)
8-14. CA. 44: 4412d (1950).
Leuckart mechanisms
M.L. Moore, The Leuckart reaction. Org. React., 5 (1949) 301-330. CA. 44: 553c (1950) .
Ephed rine reductions
K. Kindl er, B. Hedemann and E. Scharfe, Study of mechani sms of chemical reaction . X,
Phenyl and cyclohexyl-alkyl amines by hydrogenation . Justus Liebigs Ann. Chern ., 560
( 1948) 215-221. CA. 43: I 025g (1949) .
Oxime reductions
K. Kindler, B. Hedemann and E. Scharfe, A stud y of mechani sms of chemical reactions. X.
Phenyl and cyclohexyl-alkylamine by hydrogenation . Justus Liebigs Ann. Chern. , 560
(1948) 215-221. CA. 43: 1025h (1949).
Schiff base reductions
255
 References
E.R. Alexander and A.L. Misegades, A low pressure reductive alkylation method for the
conversion ofketones to primary amines. 1. Am. Chem. Soc., 70 (1948) 1315-1316. CA.
42 : 5411d (1948).
Leuckart mechanisms
E.R. Alexander and R.B. Wildman, Studies on the mechanism of the Leuckart reaction . 1.
Am. Chem. Soc., 70J1948) 1187-1189. CA. 42: 7263eJl948).
Phenylacetic acid
A.1. Vogel , A Textbook of Practical Organic Chemistry, 1st Edition (Longmans, Green and
Co.), 1948, London,_pp. 698-700 and 336-338.
Schiff base reductions
D. Shiho, A new process of alkylation of amines. 1. Ch em. Soc. Jpn., 65 (1944) 237-239.
C.A. 41: 3799i (1947).
Schiff base reduced (P-2-P + MeNH 2) to methamphetamine
D. Shiho, Anew process of alkylation of amines. 1. Chem. Soc. Jpn., 65 (1944) 135-140.
C.A. 41: 3800c (1947).
H.G. Walker and CR. Hauser, Synthesis of methyl ketones from diethyl acylmalonates. 1.
Am. Ch em. Soc. , 68 (1946) 1386-1388. CA. 40: 5712 (1946) .
Leuckart mechanisms
F.S. Crossley and M.L. Moore, Studies on the Leuckart reaction. J. Org. Chem., 9 (1944)
529-536. CA. 39: 1147 6 (1945).
Ephedrine reduction
K.W. Rosenmund, E. Karg and F.K. Marcus, Concerning the preparation of beta-Aryl-
Alkyl-amines. Berichte, 75B (1942) 1850-1859. CA. 38 : 1219 (1944).
Ephedrine reduction
K.W . Rosenmund, E. Karg and F.K. Marcus, Concerning the preparation of beta-Aryl-
Alkyl-amines. Berichte, 75B (1942) 1850-1859. CA. 38 : 1219 (1944).
Oxime reductions
F.M. Jaeger and lA. van Dijk, Preparation of2-phenylisopropylamine. Proc. Acad. Sci.
Amsterdam , 44 (1941) 26-40. CA. 37: 621 9 (1943).
P.L. Julian, J.J . Oliver, R.H. Kimball , A.B. Pike and G.D. Jefferson, 2-Phenylaceto-
acetonitrile (acetobenzyl cyanide). Org. Synth., 18 (1984) 54-55 and 66-69. C.A. 36 : 2531
(1942). Org. Synth Coli., Vol. II (1943)487-489.
B.R. Bobranski and Y.V. Drabik, Anew method of 1-phenyl-2-aminopropane preparation.
1. Appl. Chem. (U.S.S.R.), 14 (1941) 410-414. CA. 36: 2531 (1942).
Phenylacetic acid
R.M. Herbst and R.H . Manske, Methyl benzyl ketone (phenylacetone). Org. Synth., 16
(1936) 47-50. CA. 30: 3807 (1936) Org. Synth. Coli., Vol. II (1943) 389-391.
alpha-Bromobenzyl Methyl ketone intermediate
H. Erlenmeyer and M. Simon, Investigation in structure chemistry VI. Concerning a
reductive cleavage of 5-phenyl-4-methylthiazole. Helv. Chim. Acta, 25 (1942) 528-530.
CA. 36: 6539 5 (1942).
Reduction of a benzylic alcohols
(a) T. Ho and CM. Wong, Synthesis 161 (1975). (b) W.E. Parkam and Y.A. Sayed,
Sy nthesis, 116 (1976). (c) K.N.F. Shaw, M.D. Armstrong and A. McMillan, 1. Org. Ch em.,
21 (1956) 1149-1151. (d) A.C Cope et aI. , 1. Am. Chem. Soc. , 84 (1962) 2170. (e) W.
Reusch and R. LeMahiem, 1. Am. Chem. Soc., 86 (1964) 3068. (t) CA. Marvel , F.D. Hagar
and E.C Caudle, Org. Synth ., Coli., Vol. 1,224-225. © 1941.
Leuckart reactions
O.Y. Magidson and G.A. garkuska, Synthesis of beta-phenyl-isopropylamine. 1. Gen.
Chem. (U.S.S.R.), 11 (1941) 339-343. CA. 35: 5869 5 (1941).
Phenylacetic acid
o .Y. Magidson and G.A. Garkuska, Synthesis of phenyl-i sopropyl amine (Phenamine). 1.
Appl. Chem. (U .S.S.R.), 11 J1941) 339-343. CA. 35: 5868 5 (1941).
Leuckart reactions
B.R. Bobranskii and Y.K. Drabik, A new method of l-phenyl-2-aminopropane preparation.
1. Appl. Chem. (U.S.S.R.), 14 (1941) 410-414. CA. 36: 2531 9 •
Schiff base reductions
L. Haskelberg, Aminative reduction ofketones. 1. Am. Ch em. Soc., 70 (1948) 2811-2812 .
CA. 43: 1349f(1940).
256
 References
Schi ff base reductions
A. Nove lli, Sympathicomimetics, preparation of nitrogen-substituted beta-
R
phenylisopropylamines. Anal. Assoc. Quim. Argentina 27 ( 1939) 169-171. C.A. 23 : 1627
(1940).
J.P. Mason and L.1. Terry, Preparation of phenyl acetone. J. Am. Chem. Soc., 62 (1940)
1622. C.A. 34: 6248 2 (1940).
Oxime reductions
W. Leithe, Configuration of ephedrine bases. Berichte. 65 (1932) 660-666. C.A. 26: 3495
( 1932).
Chloro analogs of phenylpropanolamines
W.H . Hartung and J.c. Munch, Amino Alcohols. VI. The preparation and
pharmacodynamic activity of four isomeric phenylpropylamines. J. Am. Chem. Soc .. 53
(1931) 1875-1879 C.A. 25 : 3635 (1931).
Chloroephedrine reductions
W. Leithe, Configuration of the ephedrine bases. Berichte. 65 (1932) 660-666. C.A. 26 :
3495 .
Oxime reductions
D.H . Hey, dl-Phenylisopropylamine and related compounds. J. Chem. Soc. (1930) 18-21.
C.A . 24: 1851 (1930).
Bromo and chloro ephedrine reductions
H. Emde, Concerning diastereoisomers I. Configuration of ephedrine. Helv. Chem. Acta,
12 ( 1929) 365-376. C.A. 23: 3452-3454 (1929) .
Nitrile reductions
W.H . Hartung, Catalytic reduction of nit riles and oximes. J. Am. Ch em. Soc .. 50 ( 1928)
3370-3374. C.A. 23: 599 (1929).
2-keto oxime reductions
R.H .F. Manske and T.B. Johnson, Synthesis of ephedrine and structurally similar
compounds. I. J. Am. Chem . Soc .. 51 (1929) 580-582 . C.A . 23: 1404 (1929).
Schi ff base reductions
A. Ogata, Constitution of ephedrine. Desoxyephedrine . J. Pharm. Soc. Jpn .. 451 (1919)
75 1-764. C.A. 14: 745 (1920).
Leuckart reactions
A. Ogata, alpha and beta-Aminoalkyl(aryl)benzenes and their derivatives. J. Pharm.
Soc. Jon. 445 (1919) 193-216. CA. 13: 1709 (1919).
M. Tiffeneau, Transformation of magnesium deri vatives of chlorohydrins. Ann. Chim.
Phys .. 10(1907)322-378. c.A. 2: 265 (1908).

Leuckart to N-formylamphetamines
O . Cervinka, E. Kroupova and O. Belovsky, Asymmetric Reactions. XIX. Absolute
configu-ration of 1-phenyl-2-alkylamines and their N-methy1 derivatives. Coli. Czech.
Ch em. Commun .. 33(11) 3551-3557. C.A. 70: 37323d.
Phenylacetic acid
A.1. Vogel, Textbook of Practical Organ ic Chemistry. 1st Ed ition (Longmans, Green and
Co.) London, 1948, pp. 722-723 and 727-728.

H. Maarse, E. A. Visscher, Volatile compounds in Foods. Qualitative Data, TNO-Di vision

for nutrition and food research TNO-CIVO Food Analysis In stitute, Zeist (Netherlands)
1983 - 1987.
D. Zander (F. Encke, G . Buchheim, S. Seybold ed.): Handw6rterbuch der Pjlanzennamen.
13th ed. , Verlag E. Ulmer, Stuttgart 1984.
K. Formazek, K. H. Kubeczka, Essential Oil Analysis by Capillary Chromatography and
Carbon-13 NMR Spectroscopy. J. Wiley & Sons, New York 1982.
B. Lawrence, Progress in Essential Oils. bimonthl y column in Perfum. and Flavor. b)
Miltitzer Berichte, collection of bri ef reports on essential oils, fl avors, and fragrances ,
publi shed annually, VEB Chemisches Werk Miltitz, Miltitz (German Democratic
Republic).
Essential Oil Association of the United States No . 98.
1. Carlsson A. , Lindqvi st M., Wysokowski J., Corrodi H. , Junggren U.: Acta Pharm. Suec.
7, 293 (1970); Chern. Abstr. 73 ,64 633 (1970).
257
 References
2. Carlsson P. A. E., Junggren U. K., Hallhagen S. G., Corrodi H. R.: (Aktiebolag. Hassle):
Neth. Appl. 69/5061; Ger. Offen. I 915 230 (Swed. Appl. I. IV. 1968); Chern. Abstr. 72,
121 177 (1970).
14. Kloppel E.: Ber. Deut. Chern. Ges. 26, 1733 (1893).
15. Giacolone A.: Gazz. Chim. Ital. 65, 840 (1935); Chern. Zentr. 1936, 1, 3137.
16. Ahrens F.: Z. Chern. 1869, 104.
17. Vongerichten E., Rossler W .: Ber. Deut. Chern. Ges.lI, 705 (1898).
20. Julian P. L., Oliver J. J., Kimball R. H., Pike A. 8., Jefferson G. D.: Org. Syn. Coil.
Vol. 2. 487 (1943). 21. Ruggli P., Weis P., Rupe H.: Helv. Chirn. Acta 29,1788 (1946).
Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-
aminopropane and 5-methoxy-6-methyl-2-aminoindan: simi larities to 3,4-
(methylenedioxy)methamphetamine (MDMA).
J Med Chern, May I, 1991; 34(5): 1662-8.

258
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