Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 4
79
Views
22
CrossRef citations to date
0
Altmetric
Original Articles

Phase Transfer Catalysis: Reaction of 4-Bromopyridine with Cyclic Secondary Amines

&
Pages 251-253 | Received 08 Sep 1978, Published online: 05 Dec 2006
 

Abstract

Our interest in the acylation of alcohols lead us to investigate the use of substituted amino-pyridines as catalyst1 for the acylation reaction. Since a literature search2–5 revealed that the available procedures required the use of expensive starting materials, high temperatures, and long reaction times to obtain moderate yields of product, we investigated the applicability of phase transfer catalysis to the alkylation of several cyclic secondary amines with halopyridines. Although the alkylation of hydroxyl, thiol and amino groups using phase transfer catalyst6 is not unique, there are few examples available of the alkylation of amino groups by halogenated aromatics. We report here the alkylation of several secondary cyclic amines with 4-bromopyridine hydrochloride employing benzyltriethylammonium bromide as the phase transfer catalyst. The resulting crystalline products are powerful catalyst for the acylation of cholesterol and of

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.