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

HRID 223265ノート

反応式

HRID 223265 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-11c789af77164c3e95c1fe0087bc6bf8
出典データセット
uspto-grants-1982_10
特許番号
US04352811

反応ノート

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