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

33 g of N-benzyl-N-methyl-2-aminoethanol were dissolved in 300 ml of dichloromethane. 48 g of thionyl chloride and 2 drops of dimethylformamide were added to the solution at 0° C. The reaction mixture was then heated under reflux for 6 hours. The reaction mixture was worked up by evaporating it to dryness and taking up the residue three times in 300 ml portions of toluene and again evaporating to dryness. The remaining residue was dissolved in dichloromethane and the N-benzyl-N-(2-chloroethyl)-N-methylamine hydrochloride was crystallized by addition of diethyl ether to the solution. The crystals (m.p. 142° C.-145° C.) were filtered out and dissolved in ice water. The solution was adjusted to alkaline pH 9 by addition of aqueous sodium hydroxide solution and then extracted with toluene. The organic phase was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. 29 g of N-benzyl-N-(2- chloroethyl)-N-methylamine were obtained as a residue.

1. temperatureThe reaction mixture was then heated
2. temperatureunder reflux for 6 hours
3. customby evaporating it to dryness
4. customagain evaporating to dryness
5. dissolutionThe remaining residue was dissolved in dichloromethane
6. customthe N-benzyl-N-(2-chloroethyl)-N-methylamine hydrochloride was crystallized by addition of diethyl ether to the solution
7. filtrationThe crystals (m.p. 142° C.-145° C.) were filtered out
8. dissolutiondissolved in ice water
9. additionby addition of aqueous sodium hydroxide solution
10. extractionextracted with toluene
11. customThe organic phase was separated
12. dry with materialdried over sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure

ORDレコード

ord-ab2537e535ec47f8af68b8af48329d29

出典データセット

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05212173