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black viscous product on 800 g cracked ice and let stand three
hours, or until no more precipitation to get title compound. Filter
(recrystallize-methanol).
Simple methods of preparing phenylacetonitrile from diazoacetonitrile and triphenylboron are given in JACS 90,6891(1968) and
from the borophenyl-9-borabicyclo (3.3.1) nonane (BBN) and Clacetonitrile in JACS 91,6854(1969). These methods should work
with substituted phenyl compounds to give mescaline and analogs.
Likewise (JACS 90,5936(1968)), a preparation of phenylketones
from triphenylboron or BBN and diazoacetone, or bromo-acetone
(JACS 91,6852(1969)) may be used to prepare the phenylacetones
which can be reduced to the amphetamines in one step as already
described. For synthesis of BBN see JACS 91,4304(1969) and for
borabicyclononane see JACS 90,5280(1968).
The amphetamine and mescaline analogs which can be obtained
by replacing carbon atoms with 0 , N, or S atoms may also be
active, but little work has been done on this. For the synthesis of
thienyl analogs see JACS 64,477(1942).

Psychopharmacology Communications 1,93(1973)
MDA Japanese Patent 8573 (5 Oct 1956)

Other Syntheses
N-Methyl Mescaline HCA 35,1577(1952)
p-Methylephedrine Pharmazie 24,735(1969)
4-Nitropropenylbenzene G O 100,846(1970)
Amphetamines and Phenylethylamines JMC 11,186(1968), 13,
26,134(1970); JOC 19,11(1954), 20,102,1292(1955), 22,331
(1957), 23,1979,2034(1958), 25,2066(1960); Alab. J. Med. Sci.
1,417(1964); JCS 18(1930); BSC 835(1962); BER 63,3029
(1930), 65,424(1932), 67,696(1934); CA 6953(1964); Arznei.
Forsch. 9,157(1959); J A C S 51,2262(1929), 63,602(1941),
76,5555(1954); Pharmazie 22,19(1967); C T 3,313(1968).
Bromoamphetamines JMC 15,413(1972)
N-substituted mescaline derivatives and methamphetamine analogs
Diss. Abst. Int. 32B,5704,5706(1972).
Methamphetamine analogs JMC 16,14(1973), MMDA CJC 46,75
(1968).
See C T 8,308(1973) f o r a route from phenethyl o r phenylpropylchlorides to the amines. For older MDA syntheses see JACS
62,425(1940); JCS 15(1943), 1527(1951).
For other compounds related to STP see CJC 51,1402(1973), and
92

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