Hydrochloric Acid → 2-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)

HRID 628786

반응식

HRID 628786 반응식
[CH:1]1[C:6]([C:7]#[N:8])=[CH:5][C:4]2[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[CH:24][C:25]5[O:30][C:29]([C:31]([NH2:33])=[O:32])=[CH:28][C:26]=5[CH:27]=4)[CH2:18][CH2:17]3)=[CH:10][NH:11][C:3]=2[CH:2]=1.[ClH:34]>CC(O)C>[CH:1]1[C:6]([C:7]#[N:8])=[CH:5][C:4]2[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:23]=[CH:24][C:25]5[O:30][C:29]([C:31]([NH2:33])=[O:32])=[CH:28][C:26]=5[CH:27]=4)[CH2:20][CH2:21]3)=[CH:10][NH:11][C:3]=2[CH:2]=1.[ClH:34]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 6918314Vilazodone2회

생성물 1

HCID 69183132-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

Similar process for the preparation of vilazodone is also reported in Journal of Medicinal Chemistry, 2004, Vol. 47, No. 19, pages 4684-4692 (hereinafter referred to as the ‘JMC article’). As per the process reported in the JMC article (see column-1 of Page No. 4690), the vilazodone is prepared by reacting 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxylic acid with 2-chloro-1-methylpyridinium iodide in the presence of N-methylpyrrolidone to produce a reaction mass, followed by drop wise addition of ethyldiisopropyl amine while introducing ammonia gas and subsequent work up to produce vilazodone. The resulting vilazodone free base is then converted into its hydrochloride salt by dissolving vilazodone free base in hot 2-propanol to form a solution, followed by slow addition of HCl-saturated 2-propanol at room temperature until complete precipitation occurs to yield vilazodone hydrochloride (Melting Point: 277-279° C.).

후처리

  1. customto form a solution

출처 및 근거

ORD 기록
ord-6bb285fae27d42dba141766814a4fff9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315456B2

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