Benzyl Bromide → N-Benzylnormechlorethamine

HRID 1110046Notes

Reaction equation

HRID 1110046 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([N:5]([CH2:6][CH2:7][Cl:8])[CH2:4][CH2:3][Cl:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 5928N-BenzylnormechlorethamineYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of bis (2-chloroethyl) amine hydrochloride (150 g, 0.84 mol), potassium carbonate (255 g, 1.9 mol) and benzyl bromide (110 ml, 0.92 mol) in DMF (1500 ml) was heated at 100° C. for 1 hour. The mixture was allowed to cool to ambient temperature, then the DMF removed in vacuo. The residue was taken into ethyl acetate (1000 ml), then washed with water (2×1000 ml). The organic phase was separated, dried (MgSO4) and evaporated. The crude residue was chromatographed in 20:1 petrol:ether, to give N-benzyl bis(2-chloroethyl)amine (36 g, 18%) as a pale yellow oil.

Workup

  1. customthe DMF removed in vacuo
  2. washwashed with water (2×1000 ml)
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude residue was chromatographed in 20:1 petrol

Sources & evidence

ORD record
ord-ded51030e00940dcae1cddbf1da56a2c
Source dataset
uspto-grants-1994_06
Patent number
US05324733

Reaction notes

Loading…