Dimethylformamide → HCID 86738587, compound

HRID 223265Notes

Reaction equation

HRID 223265 reaction equation
[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

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13076426HCID 13076426, compoundHCID 134509002-Methyl-3-(phenylsulfonylpropyl)indole

Product 1

HCID 86738587HCID 86738587, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-11c789af77164c3e95c1fe0087bc6bf8
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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