Benzyl Bromide → N-Benzylnormechlorethamine

HRID 29862

Reaction equation

HRID 29862 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

An ice bath is used to cool a mixture of 150 g of N,N-bis(2-chloroethyl)amine hydrochloride and 100 ml of benzyl bromide in 1000 ml of DMF and then 120 ml of triethylamine are added dropwise and the mixture is left with stirring at AT overnight. The reaction mixture is concentrated under vacuum, the residue is taken up in 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. customAn ice bath is used
  2. temperatureto cool
  3. waitthe mixture is left
  4. concentrationThe reaction mixture is concentrated under vacuum
  5. extractionextracted 3 times with ether
  6. dry with materialthe organic phases are dried over Na2SO4
  7. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-a9bfd6e512c14c1f87f97806cb513292
Source dataset
uspto-grants-2008_09
Patent number
US07423039B2

Linked notes

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