Benzyl Bromide → N-Benzylnormechlorethamine

HRID 1993296Notes

Reaction equation

HRID 1993296 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>[Cl:2][CH2:3][CH2:4][N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7][Cl:8]

Participants

5

Reactant 3

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

Product 1

HCID 5928N-Benzylnormechlorethamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using an ice bath, a mixture of 150 g of N,N-bis(2-chloroethyl)amine hydrochloride and 100 ml of benzyl bromide in 1000 ml of DMF is cooled and then 120 ml of triethylamine are added dropwise and the mixture is left overnight with stirring at AT. The reaction mixture is concentrated under vacuum, the residue is taken up with water and extracted 3 times with ether, the organic phases are dried over Na2SO4 and the solvent is evaporated under vacuum. This gives 113 g of the expected product.

Workup

  1. temperatureis cooled
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. extractionextracted 3 times with ether
  4. dry with materialthe organic phases are dried over Na2SO4
  5. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-a1e59e7587e643c0bebd7d0abbfbbe2f
Source dataset
uspto-grants-2010_01
Patent number
US07652011B2

Reaction notes

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