Benzyl Bromide → N-Benzylnormechlorethamine

HRID 1966116Notes

Reaction equation

HRID 1966116 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[Cl:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][Cl:22]>C(#N)C>[CH2:7]([N:19]([CH2:20][CH2:21][Cl:22])[CH2:18][CH2:17][Cl:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

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

Product 1

HCID 5928N-BenzylnormechlorethamineYield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

21 g (152 mmol) of potassium carbonate and then 8 ml (67 mmol) of benzyl bromide are added to a solution of 10 g (56 mmol) of bis(2-chloroethyl)amine hydrochloride in 130 ml of acetonitrile, and then the reaction medium is heated at 60° C. for 24 h. After filtration, the filtrate is concentrated under vacuum. The crude residue is purified by chromatography on silica gel, elution being carried out with a 90/10 heptane/ethyl acetate mixture, to give 8.5 g (65%) of benzylbis(2-chloroethyl)amine.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe crude residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-e34da6e4b23549dca678b257775a1853
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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