Dimethylformamide → 4-(Diphenylmethyl)-1-piperazineethanol

HRID 746241

Reaction equation

HRID 746241 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH:21](Br)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH:21]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][OH:9])[CH2:2][CH2:3]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 47425734-(Diphenylmethyl)-1-piperazineethanolYield 84.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-piperazineethanol (11.4 g), potassium carbonate powder (24.3 g) and N,N-dimethylformamide (100 ml) was added dropwise benzhydryl bromide (21.7 g). The mixture was stirred at room temperature for 2 hours, then diluted with water and extracted with ethyl ether. The ethyl ether layer was washed with saturated aquus sodium chloride and dried over sodium sulfate. The solvent was then distilled off and the residue was purified by silica gel chromatography [eluent: hexane-ethyl acetate (2:1)] to give 21.9 g (84.2%) of 4-benzhydryl-1-piperazineethanol as an oil.

Workup

  1. extractionextracted with ethyl ether
  2. washThe ethyl ether layer was washed with saturated aquus sodium chloride
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was then distilled off
  5. customthe residue was purified by silica gel chromatography [eluent: hexane-ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-a7f89949a20b48bfbffc559b3f3b5a68
Source dataset
uspto-grants-1986_07
Patent number
US04603135

Linked notes

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