Thionyl Chloride → N-benzyl-2-chloro-N-methylethanamine

HRID 622173Notes

Reaction equation

HRID 622173 reaction equation
O[CH2:2][CH2:3][N:4]([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(Cl)([Cl:15])=O>>[Cl:15][CH2:2][CH2:3][N:4]([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 66876N-Benzyl-N-methylethanolamine

Product 1

HCID 31968N-benzyl-2-chloro-N-methylethanamine

Procedure

N-(2-hydroxyethyl)-N-benzyl-methylamine is a known compound and is described in literature (J. Am. Chem. Soc. 76, 4920-23, 1954). The reaction of this compound with thionyl chloride gives N-(2-chloroethyl)-N-benzyl-methylamine in a good yield. This compound can also be prepared by reacting N-benzyl-methylamine with 1-bromo-2-chloroethane, the yields, however, are poor and the dimeric 1,2-bis(N-benzylmethylamino)ethane, which is formed as a by-product, must be separated by chromatography.

Sources & evidence

ORD record
ord-0aa07242f8b246fbab0d18d37b07b52c
Source dataset
uspto-grants-1988_09
Patent number
US04769465

Reaction notes

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