An improved synthesis of butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224)

Citation
J. Sakaguchi et al., An improved synthesis of butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate (AU-224), CHEM PHARM, 49(6), 2001, pp. 788-790
Citations number
7
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
49
Issue
6
Year of publication
2001
Pages
788 - 790
Database
ISI
SICI code
0009-2363(200106)49:6<788:AISOB4>2.0.ZU;2-S
Abstract
A new and facile route for the synthesis of the novel gastrointestinal prok inetic butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineaceta te (1b), which exhibited potent gastro- and colon-prokinetic activities by oral administration without significant side effects, was established. The key intermediate, butyl 4-amino-1-piperidineacetate (16), was prepared from commercially available 4-amino-1-benzylpiperidine (2) in a high yield with four steps. Compound 1b was prepared by condensation of commercially avail able 4-amino-5-choloro-2-methoxybenzoic acid (7) with 16 in 84% yield. This improved synthetic route was appropriate for large-scale synthesis of 1b.