Benzyl Bromide → N-Benzylnormechlorethamine
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>C(#N)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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Bis-(2-chloro-ethyl)-amine hydrochloride was suspended in 150 mL acetonitrile. Added were 34.8 g K2CO3 (3 equiv.) and 10.0 mL benzylbromide (1 equiv.). The mixture was refluxed overnight, Concentration on silica and purification with flash column chromatography (eluents PA:ether=95:5) yielded 4.11 g of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 2.93 (t, J=7 Hz, 4H), 3.50 (t, J=7 Hz, 4H), 3.74 (s, 2H), 7.22-7.37 (m, 5H).
Workup
- additionAdded
- temperatureThe mixture was refluxed overnight
- concentrationConcentration
- customon silica and purification with flash column chromatography (eluents PA:ether=95:5)
Sources & evidence
- ORD record
- ord-bb9528bd65444948971ae1d9ea7916a5
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728018B2
Reaction notes
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