Accession Number:

AD0603454

Title:

MERCAPTOPIPERIDINES.

Descriptive Note:

Final rept. for Sep 62-Sep 63,

Corporate Author:

NEW HAMPSHIRE UNIV DURHAM

Personal Author(s):

Report Date:

1964-06-15

Pagination or Media Count:

16.0

Abstract:

The synthesis of 3- and 4-mercaptopiperidines derivatives by nucleophilic displacement by a sulfur nucleophile was impractical since 3- and 4-halopiperidines give anomolous reactions under solvolytic conditions. Alternate approaches to the mercaptopiperidines by reduction of gem-dithiols, ionic and free-radical additions of RSH, and the Asinger reaction were attempted. The prepa ration of 1-methyl-4-mercaptopiperidine was achieved from 1-methyl-4-piperidine via the gem-dithiol intermediate. The addition of thiolacetic acid, hydrogen sulfide, and benzyl mercaptan to 1-methyl-1, 2, 3, 6-tetrahydropyridine failed as a method of synthesis of mercaptopiperidines. The Asinger reaction with 1-methyl-4-piperidone was successful in introducing a sulfur-substituent at the 3position of piperidine. The desired derivative of 3-mercaptopiperdine could not be isolated, however. Author

Subject Categories:

Distribution Statement:

APPROVED FOR PUBLIC RELEASE