Process for preparing a ketimine

Details Process for preparing a ketimine Process for preparing a ketimine

1988-05-04

1989-08-08

Reamer, James H.

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

Organic compounds

Amino nitrogen containing

C07C11914

Patent

active

048555002

ABSTRACT:
An improved condensation process for preparing N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine from 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone and methylamine is disclosed. The process involves the use of a hydratable molecular sieve having a pore size that is at least about three Angstrom units in diameter as the dehydrating agent (catalyst) in a reaction-inert aprotic organic solvent. The ketimine final product so produced is known to be useful as an intermediate leading to cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal enamine (sertraline), which is an anti-depressant agent.

REFERENCES:
patent: 4536518 (1985-08-01), Welch, Jr. et al.
W. M. Welch, Jr. et al., Journal of Medicinal Chemistry, vol. 27, No. 11, p. 1508 (1984).
E. P. Kyba in Organic Preparations and Procedures, vol. 2(2), p. 149 (1970).
K. Taguchi et al., in the Journal of Organic Chemistry, vol. 36, p. 1570 (1971).

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