Chloroform → 2-Chloro-N-(2-chloroethyl)-N-(2-phenylethyl)ethan-1-amine--hydrogen chloride (1/1)

HRID 374460Notes

Reaction equation

HRID 374460 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]([CH2:13]CO)[CH2:10][CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O.[CH:20]([Cl:23])(Cl)Cl>>[ClH:18].[C:1]1([CH2:7][CH2:8][N:9]([CH2:13][CH2:20][Cl:23])[CH2:10][CH2:11][Cl:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 24386Thionyl ChlorideHCID 10987515Ethanol, 2,2'-[(2-phenylethyl)imino]bis-

Product 1

HCID 189332272-Chloro-N-(2-chloroethyl)-N-(2-phenylethyl)ethan-1-amine--hydrogen chloride (1/1)

Procedure

To a solution of 20.0 g (95 mmoles) of N-(2-phenylethyldiethanolamine in 40 mL of chloroform was added, over a period of 1 hour, 20 mL of thionyl chloride in 20 mL of chloroform. The mixture was heated under reflux for 2 hours and concentrated to give N-(2-phenylethyl)-N,N-bis(2-chloroethyl)amine hydrochloride as an oil. NMR (CDCl3) δ7.2-7.4 (m, 5H); 4.1 (t, 4H); 3.6 (t, 4H); 3.5 (m, 2H) and 3.2 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eee0cbb413c845eeb4676a1f02e2ae68
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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