Dimethylformamide → 3-(4-[5,6-Dimethoxy-1,2-benzisoxazol-3-yl]piperidyl}-2-methyl indole

HRID 223265노트

반응식

HRID 223265 반응식
[CH3:1][O:2][C:3]1[C:4]([O:18][CH3:19])=[CH:5][C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:7]=2[CH:17]=1.[CH3:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1CCCS(C1C=CC=CC=1)(=O)=O)=[CH:27][CH:26]=[CH:25][CH:24]=2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]1[C:4]([O:18][CH3:19])=[CH:5][C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:12][CH2:13][N:14]([C:29]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][C:21]=4[CH3:20])[CH2:15][CH2:16]3)[C:7]=2[CH:17]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 130764265,6-Dimethoxy-3-(4-piperidyl)-1,2-benzisoxazoleHCID 134509002-Methyl-3-(phenylsulfonylpropyl)indole

생성물 1

HCID 867385873-(4-[5,6-Dimethoxy-1,2-benzisoxazol-3-yl]piperidyl}-2-methyl indole수율 26.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A stirred mixture of 5.0 g of 5,6-dimethoxy-3-(4-piperidyl)-1,2-benzisoxazole, 6.78 g of 2-methyl-3-(phenylsulfonylpropyl)indole, 120 ml of dimethylformamide and 15.0 g of anhydrous potassium carbonate was heated to 90° for 6 hrs and overnight at ambient temperature. The mixture was poured into water (300 ml) and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield a solid. The solid was purified by passing it through a silica gel column (20:1) and eluting it with dichloromethane-methanol (1%). Recrystallization two times from ethanol-water yielded 2.0 g (24%) of product, mp 176°-178°.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customto yield a solid
  5. customThe solid was purified
  6. washeluting it with dichloromethane-methanol (1%)
  7. customRecrystallization two times from ethanol-water

출처 및 근거

ORD 기록
ord-11c789af77164c3e95c1fe0087bc6bf8
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04352811

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