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

HRID 542201

Reaction equation

HRID 542201 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, 9.5 g (0.24 mol) of sodium hydroxide and 5 ml of water are stirred together for 1 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. Vacuum distillation of the yellow oil obtained 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. distillationVacuum distillation of the yellow oil
  5. customobtained

Sources & evidence

ORD record
ord-d75c00d5d21d4a309628e8166038e4f5
Source dataset
uspto-grants-1987_04
Patent number
US04656180

Linked notes

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