Dimethylformamide → HCID 12262052, compound

HRID 746244Notes

Reaction equation

HRID 746244 reaction equation
[CH2:1](Br)[CH2:2][OH:3].[C:5]1([CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:19]1([CH:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:1][CH2:2][OH:3])[CH2:17][CH2:18]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 12262036HCID 12262036, compound

Product 1

HCID 12262052HCID 12262052, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethylene bromohydrin (4.03 g) was added dropwise to a mixture of 1-(2,2-diphenylethyl)piperazine (4.30 g), potassium carbonate (6.7 g) and N,N-dimethylformamide (20 ml) with stirring. The mixture was stirred at room temperature overnight, diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over Na2SO4. The solvent was then distilled off and the residue was subjected to silica gel chromatography. Elution with ethyl ether-ethyl acetate-methanol (10:2:1, v/v) gave 4-(2,2-diphenylethyl)-1-piperazineethanol as an oil. Yield 4.24 g.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over Na2SO4
  5. distillationThe solvent was then distilled off
  6. washElution with ethyl ether-ethyl acetate-methanol (10:2:1

Sources & evidence

ORD record
ord-a27cb6f260214ac8b54bc16287b72a49
Source dataset
uspto-grants-1986_07
Patent number
US04603135

Reaction notes

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