Propylamine → HCID 20081636, compound

HRID 1609466Notes

Reaction equation

HRID 1609466 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][C:11]([OH:13])=[O:12])[CH:5]=O.[CH2:14]([NH2:17])[CH2:15][CH3:16].ClC1[N:24](C)[C:23]2[CH:26]=[CH:27][CH:28]=[CH:29]C=2S(=O)(=O)N=1>>[C:11]([CH2:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][N:24]2[CH2:23][CH2:26][CH2:27][CH2:28][CH2:29]2)=[CH:3][C:2]=1[O:1][CH2:16][CH2:15][CH2:14][NH2:17])([OH:13])=[O:12]

Participants

4

Reactant 3

HCID 7852PropylamineHCID 1986904H-1,2,4-Benzothiadiazine, 3-chloro-4-methyl-, 1,1-dioxideHCID 20081638HCID 20081638, compound

Product 1

HCID 20081636HCID 20081636, compoundYield 24%

Procedure

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.

Workup

  1. customobtained in Reference Example 4 in the same manner as in Example 1
  2. customThe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c52c603a13f44de695dafa70d95b072f
Source dataset
uspto-grants-1995_03
Patent number
US05401739

Reaction notes

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