Propylamine → HCID 20081636, compound

Participants

Reaction Steps

3-[2-Carboxymethyl-5-(piperidinomethyl)phenoxy]propylamine was prepared by the same procedures as in Reference Example 1 and Example 1 using 3-hydroxy-4-carboxymethylbenzaldehyde in place of the 3-hydroxybenzaldehyde used in Reference Example 1. This propylamine was reacted with the 3-chloro-4-methyl-1,2,4-benzothiadiazine-1,1-dioxide obtained in Reference Example 4 in the same manner as in Example 1. The reaction mixture was purified by silica gel column chromatography using chloroform:methanol (20:1) to isolate 3-[N-[3-[2-carboxymethyl-5-(piperidinomethyl)phenoxypropyl]-N-(4-methoxybenzyl)]amino]-4-methyl-1,2,4-benzothiadiazine-1,1-dioxide in a yield of 24%. The product was dissolved in ethyl acetate, and a solution of 4N hydrochloric acid and ethyl acetate was added dropwise to the solution with ice cooling to obtain a white crystalline hydrochloride. Thus, a compound 27 listed in Table 1 was prepared in a yield of 75%. M.p.: 93°~97° C.

Provenance & Evidence