Chloroform → N,N-dibenzyl-1-(oxiran-2-yl)methanamine

HRID 542785

Reaction equation

HRID 542785 reaction equation
Cl[CH2:2][CH:3]([OH:20])[CH2:4][N:5]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].C(Cl)(Cl)Cl>O>[CH2:6]([N:5]([CH2:4][CH:3]1[CH2:2][O:20]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 135354791-Chloro-3-dibenzylamino-2-propanol

Product 1

HCID 11276836N,N-dibenzyl-1-(oxiran-2-yl)methanamineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

50.7 g (0.175 mol) of 1-chloro-3-dibenzylamino-2-propanol and 9.5 g (0.24 mol) of sodium hydroxide in 5 ml of water are stirred together for one hour at 95° c. After the addition of 50 ml of chloroform and 20 ml of water, the phases are separated and the organic phase is washed with 20 ml of water, dehydrated with sodium sulphate and concentrated by evaporation. Distillation of the resulting yellow oil under vacuum yields 33.7 g (76%) of the oxirane as a colourless oil.

Workup

  1. customthe phases are separated
  2. washthe organic phase is washed with 20 ml of water
  3. concentrationconcentrated by evaporation
  4. distillationDistillation of the resulting yellow oil under vacuum

Sources & evidence

ORD record
ord-77df8396dc084fb0a0092ea8b7aa3c41
Source dataset
uspto-grants-1987_04
Patent number
US04659721

Linked notes

Loading…