Diethyl Ether → N-Benzyl-2-chloroethan-1-amine

HRID 2049749Notes

Reaction equation

HRID 2049749 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([NH:12][CH2:13][CH2:14]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCOCC>C(Cl)(Cl)Cl>[CH2:5]([NH:12][CH2:13][CH2:14][Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4348BenzylethanolamineHCID 24386Thionyl Chloride

Product 1

HCID 22713N-Benzyl-2-chloroethan-1-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

100 ml. of thionyl chloride are added to a stirred solution of 100 g. of 2-benzylaminoethanol in 500 ml. of chloroform over a period of 20 minutes. The mixture is refluxed for 6 hours. 1350 ml. of ether is added to the cooled chloroform solution and the mixture is stored in the refrigerator overnight. The product, N-benzyl-2-chlorethylamine hydrochloride, is filtered off and crystallized from ethanol-ether; yield 130.9 g., m.p. 192°-194°.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. customis stored in the refrigerator overnight
  3. filtrationThe product, N-benzyl-2-chlorethylamine hydrochloride, is filtered off
  4. customcrystallized from ethanol-ether

Sources & evidence

ORD record
ord-bcbc2bf43154430a82877c791888a528
Source dataset
uspto-grants-1980_04
Patent number
US04198509

Reaction notes

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