Dicyclohexylcarbodiimide → 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

HRID 2295807노트

반응식

HRID 2295807 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:20]([OH:27])=[C:21]([CH2:23][C:24](O)=[O:25])[CH:22]=1>C(Cl)Cl>[Cl:16][C:17]1[C:18]([N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:19][C:20]2[O:27][C:24](=[O:25])[CH2:23][C:21]=2[CH:22]=1

참가 물질

4

반응물 2

HCID 10868DicyclohexylcarbodiimideHCID 539130445-Chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid

생성물 1

HCID 135769525-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 6.5 g (31.5 mmoles) of dicyclohexylcarbodiimide in 40 ml of absolute methylene chloride is added at room temperature in the course of approximately 3 minutes to a solution of 8.1 g (30 mmoles) of crude 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid in 50 ml of absolute methylene chloride. The reaction mixture is stirred at room temperature for 30 minutes. The precipitated dicyclohexylurea is filtered off with suction and washed with methylene chloride. The filtrate is concentrated by evaporation in a vacuum rotary evaporator and the residue is chromatographed over silica gel with the eluant methylene chloride/hexane (1:1). Recrystallisation from hexane yields 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 129°-131° C.

후처리

  1. filtrationThe precipitated dicyclohexylurea is filtered off with suction
  2. washwashed with methylene chloride
  3. concentrationThe filtrate is concentrated by evaporation in a vacuum rotary evaporator
  4. customthe residue is chromatographed over silica gel with the eluant methylene chloride/hexane (1:1)
  5. customRecrystallisation from hexane

출처 및 근거

ORD 기록
ord-1fbb8ac5ee4d41e8a7925b3bc8ba8e5d
출처 데이터셋
uspto-grants-1984_01
특허 번호
US04426380

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