Method for the preparation of 4-phenyl-1,3-benzodiazepins

Details Method for the preparation of 4-phenyl-1,3-benzodiazepins Method for the preparation of 4-phenyl-1,3-benzodiazepins

1994-09-09

1996-02-06

Bond, Robert T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D243204, A61K 3155

Patent

active

054896819

ABSTRACT:
A compound of the formula ##STR1## is prepared by reacting an N-acylated-o-toluidine of the formula ##STR2## with n-alkyllithium to form a dilithio intermediate of the formula ##STR3## which can then be quenched with N-benzylidenemethylamine to fore compound II. Hydrolysis of compound(II) yields the free base ##STR4## or its salt, which can be cyclized to form 4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine or its physiologically acceptable salts, which are useful as pharmacological agents.

REFERENCES:
patent: 3510560 (1970-05-01), Saunders
patent: 4309424 (1982-01-01), Martin et al.
patent: 5292760 (1994-03-01), Martin et al.
Muchowski et al. "Ortho Functionalization of N-(t-butoxycarbonyl)aniline," JOC 45:4798-4801 (1980).
Fuhrer et al., "Ortho Functionalization of Aromatic Amines: Ortho lithiation of N-Pivaloylanilines," JOC 44:1133-1136 (1979).
Muchowski et al., "O-Functionalization of Aromatic Amines: O-Lithiatian of N-Povaloylanilines," JOC 44:1133-1136 (1979).

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