Dimethylformamide → 4-(Diphenylmethyl)-1-piperazineethanol

HRID 329881Notes

Reaction equation

HRID 329881 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) under stirring. The mixture was stirred at room temperature for 2 hours, diluted with water and extracted with ethyl ether. The ethyl ether layer was washed with saturated aqueous sodium chloride and dried over anhydrous 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. IR(Neat): 3380 cm-1. NMR(CDCl3)δ: 2.46(10H, broad s), 3.57(2H, t, J=6.5), 4.20(1H, s), 7.03-7.45(12H, m).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl ether
  3. washThe ethyl ether layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off
  6. customthe residue was purified by silica gel chromatography [eluent: hexane-ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-0d3866aecc7e40d7b0045a2627557991
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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