Thionyl Chloride → Benzylamine, N-(2-chloroethyl)-N-methyl-, hydrochloride

HRID 1669404Notes

Reaction equation

HRID 1669404 reaction equation
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:15]>>[Cl-:15].[CH2:1]([NH+:8]([CH3:12])[CH2:9][CH2:10][Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

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

Product 1

HCID 31967Benzylamine, N-(2-chloroethyl)-N-methyl-, hydrochloride

Conditions

Temperature
35 °C

Procedure

2-[benzyl(methyl)amino]ethanol was added dropwise to an excess of SOCl2 (50 eq) and the mixture heated at 35° C. for 16 h. Volatiles were removed in vacuo and the residual oil triturated with Et2O to give the title compound as a white solid in quantitative yield. (ES+) m/z 184 (M+H)+; 186 (M+H)+.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residual oil triturated with Et2O

Sources & evidence

ORD record
ord-29ca0a6cea7045ec983d1fcf727a0324
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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