2-Bromoethanol → 1H-1,4-Diazepine-1-ethanol, 4-(diphenylmethyl)hexahydro-

HRID 329884Notes

Reaction equation

HRID 329884 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](Br)[CH2:15][OH:16].[CH:18](Br)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CN(C)C=O>[CH:18]([N:1]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:14][CH2:15][OH:16])[CH2:3][CH2:2]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 236603Bromodiphenylmethane

Product 1

HCID 122365181H-1,4-Diazepine-1-ethanol, 4-(diphenylmethyl)hexahydro-Yield 17.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of homopiperazine (5.0 g), potassium carbonate powder (13.8 g) and N,N-dimethylformamide (80 ml) was added ethylene bromohydrin (6.3 g) and the mixture was stirred at room temperature for 12 hours. Then, benzhydryl bromide (12.4 g) was added and the whole mixture was further stirred at room temperature for 6 hours, diluted with water and extracted with ethyl ether. The ethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the oily residue was purified by silica gel chromatography [eluent: chloroform-methanol (20:1)] to give 4-benzhydrylhomopiperazine-1-ethanol as an oil (2.7 g, 17.4%). IR(Neat): 3400 cm-1. NMR(CDCl3)δ: 1.6-1.9(2H, m), 2.5-2.9(10H, m), 3.08(1H, s), 3.52(2H, t, J=6), 4.57(1H, s), 7.0-7.5(10H, m).

Workup

  1. stirringthe whole mixture was further stirred at room temperature for 6 hours
  2. extractionextracted with ethyl ether
  3. washThe ethyl ether layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe oily residue was purified by silica gel chromatography [eluent: chloroform-methanol (20:1)]

Sources & evidence

ORD record
ord-228cf4ddf9cf430791bf1e707024ac4a
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

Loading…