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

HRID 266013

Reaction equation

HRID 266013 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

At 0° C., 100 g (506.9 millimoles) of dibenzylamine (dissolved in 300 ml of methylene chloride) is added dropwise to a thoroughly stirred suspension of 234.51 g (2.53 mol) of epichlorohydrin and 200 ml of 32% sodium hydroxide solution. The mixture is stirred for 2 hours at 0° C. and then 3 hours at room temperature. The mixture is diluted with 3 l of water and extracted 3 times with 500 ml of methylene chloride. The organic phases are combined, dried over magnesium sulfate, and evaporated under vacuum. The remaining oil is flash-chromatographed on silica gel (mobile phase: methylene chloride/hexane/acetone:20/10/3). Yield: 111.72 g of a colorless oil (87% of theory).

Workup

  1. custom3 hours
  2. customat room temperature
  3. extractionextracted 3 times with 500 ml of methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe remaining oil is flash-chromatographed on silica gel (mobile phase: methylene chloride/hexane/acetone:20/10/3)

Sources & evidence

ORD record
ord-23fb3ce2e1d84559b16dc85cb4ccaf41
Source dataset
uspto-grants-1997_07
Patent number
US05650136

Linked notes

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