Reaction #433632

ord-0cc9c9d9b5fb4a71ae071e7b3c235fb3

Reaction equation

CCOC(=O)CC(=O)N1CCc2ccc(OCc3cccc(F)c3)cc2CC1
3-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-3-oxo-propionic acid ethyl ester
Cl.Fc1cccc(COc2ccc3c(c2)CCNCC3)c1
7-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride
CCC(C(=O)Cl)C(=O)Cl
ethyl malonic acid chloride
NC(=O)CC(=O)N1CCc2ccc(OCc3cccc(F)c3)cc2CC1
title compound
Yield 70.0%
NC(=O)CC(=O)N1CCc2ccc(OCc3cccc(F)c3)cc2CC1
3-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-3-oxo-propionamide
Yield 70.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

3-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-3-oxo-propionic acid ethyl ester: The title compound was prepared in analogy to Example 1d) from 7-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [Example 1c)] and ethyl malonic acid chloride with triethylamine as the base. Yield: 70% of theory as a colourless oil; MS: m/e=386 (M+H)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07173023B2uspto-grants-2007_02