Preparation of 1,2,4,5-tetrahydro-7-alkoxy-(and 7,8-dialkoxy)-3H

Details Preparation of 1,2,4,5-tetrahydro-7-alkoxy-(and 7,8-dialkoxy)-3H Preparation of 1,2,4,5-tetrahydro-7-alkoxy-(and 7,8-dialkoxy)-3H

1978-11-20

1981-08-04

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

564374, C07D22316

Patent

active

042821460

ABSTRACT:
Certain 1,2,4,5-tetrahydro-7-alkoxy-(and 7,8-dialkoxy)-3H,3-benzazepines are prepared in excellent yields by a three step process comprising reacting a 3-alkoxy-(or 3,4-dialkoxy)-phenethylamine with a halo-acetaldehyde dialkylacetal to form the corresponding N-(2,2-dialkoxyethyl) phenethylamine, reacting that product with BF.sub.3 to close the ring and to form a 1-alkoxy-1,2,3,4-tetrahydro-7-alkoxy-(or 7,8-dialkoxy)-3H,3-benzazepine and reacting that product under reductive cleavage conditions to remove the 1-alkoxy group and to obtain the desired benzazepine. The benzazepines can be further reacted in the known manner or in the manner disclosed herein to form certain 3-substituted benzazepines.

REFERENCES:
patent: 3393192 (1968-07-01), Walter et al.
patent: 3686167 (1972-08-01), Fujimura et al.
Olah Friedel-Crafts and Related Reactions, p. 223, vol. I, Interscience, NY (1963).
Likforman et al., Comptes Rendus, t268, 6/30/69, pp. 2340-2341.

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