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

HRID 637682노트

반응식

HRID 637682 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 mmole) of dicyclohexyl carbodiimide in 40 ml of absolute methylene chloride is added at room temperature over a period of approximately 3 minutes to a solution of 8.1 g (30 mmole) of crude 5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenylacetic acid in 50 ml of absolute methylene chloride. The reaction mixture is stirred for 30 minutes at room temperature. The precipitated dicyclohexylurea is filtered 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 using methylene chloride/hexane (1:1) as eluant. recrystallisation from hexane yields 5-chloro-6-(piperidin-1-yl)-benzofuran-2(3H)-one having a melting point of 129°-131°.

후처리

  1. filtrationThe precipitated dicyclohexylurea is filtered 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
  5. customrecrystallisation from hexane

출처 및 근거

ORD 기록
ord-1a867f40a79f4d23a8e7480012d19c6f
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04558043

반응 노트

불러오는 중…