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

HRID 1417118Notes

Reaction equation

HRID 1417118 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.[OH-].[Na+]>O>[O:20]1[CH:18]([CH2:16][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:19]1

Participants

5

Reactant 3

HCID 7656DibenzylamineHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 11276836N,N-dibenzyl-1-(oxiran-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

100 g (506.9 mmol) of dibenzylamine (dissolved in 300 ml of dichloromethane) is instilled in a well-stirred suspension of 234.51 g (2.53 mol) of epichlorohydrin and 200 ml of 32% sodium hydroxide solution at 0° C. It is stirred for 2 hours at 0° C., then for 3 hours at room temperature. It is diluted with 3 1 of water and extracted 3 times with 500 ml of dichloromethane. The organic phases are combined, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The remaining oil is "flash"-Chromatographed on silica gel (mobile solvent: dichloromethane/hexane/acetone: 20/10/3).

Workup

  1. waitfor 3 hours at room temperature
  2. extractionextracted 3 times with 500 ml of dichloromethane
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-b98023d7c1a94260bb8e4f2fabf78715
Source dataset
uspto-grants-1999_03
Patent number
US05876698

Reaction notes

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