Thionyl Chloride → N-(2-Chloroethyl)-N-methylbenzylamine hydrochloride
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.S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[ClH:15].[CH2:1]([N:8]([CH2:9][CH2:10][Cl:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
N-Benzyl-N-methylethanolamine (200 ml) was dissolved in chloroform (600 ml). The solution was cooled to 0° C. with stirring and then thionyl chloride (100 ml) was added dropwise, with stirring, at a rate such that the temperature of the reaction mixture was kept below 15° C. The mixture was boiled under reflux for 2 hours and then evaporated to dryness. The solid residue was triturated with ether, filtered and dried to give N-benzyl-2-chloro-N-methylethylamine hydrochloride.
Workup
- stirringwith stirring, at a rate such that the temperature of the reaction mixture
- customwas kept below 15° C
- temperatureunder reflux for 2 hours
- customevaporated to dryness
- customThe solid residue was triturated with ether
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-7aaf8ee8c0f24eb8ac6b690a1b9a6149
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05736568
Reaction notes
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