Benzyl Bromide → N-Benzylnormechlorethamine

HRID 2111606Notes

Reaction equation

HRID 2111606 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:9]([N:5]([CH2:6][CH2:7][Cl:8])[CH2:4][CH2:3][Cl:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 5928N-BenzylnormechlorethamineYield 56.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 150 g of bis(2-chloroethyl)amine hydrochloride and 144 g of benzyl bromide in 1000 ml of DMF is cooled on an ice bath, 120 ml of triethylamine are added dropwise and the mixture is then stirred for 5 hours at rt. The reaction mixture is concentrated under vacuum, the residue is taken up in water and extracted with ether, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. 110 g of the expected product are obtained.

Workup

  1. temperatureis cooled on an ice bath
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionextracted with ether
  4. dry with materialthe organic phase is dried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-4c6223476b47427d9e0936071140650a
Source dataset
uspto-grants-2009_04
Patent number
US07521449B2

Reaction notes

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