N-CBZ-N,N-BIS(2-CHLOROETHYL)AMINE Chemical Properties

Boiling point:

376.9±42.0 °C(Predicted)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.78±0.70(Predicted)

Appearance

Colorless to light yellow Liquid

N-CBZ-N,N-BIS(2-CHLOROETHYL)AMINE Usage And Synthesis

Synthesis

Bis(2-chloroethyl)amine hydrochloride (5 g, 0.028 mol) was suspended in 30 ml of anhydrous dichloromethane under cooling in an ice water bath and stirring. Benzyl chloroformate (5.1 g, 0.03 mol) was added slowly dropwise with a controlled dropwise time of 10 min. Subsequently, triethylamine (6.46 g, 0.063 mol) was added dropwise over 1 hour. The reaction mixture was continued to be stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water (10 ml) and stirring was continued for 15 minutes. The organic phase (dichloromethane layer) was separated and washed sequentially with 1M HCl (10 ml) and saturated saline (10 ml), dried anhydrically and concentrated under reduced pressure to give the oily target product benzyl bis(dichloroethyl)aminocarboxylate (7 g, 95.5% yield, 80% purity).

References

[1] Organic Letters, 2009, vol. 11, # 2, p. 449 - 452
[2] Patent: US2009/143582, 2009, A1. Location in patent: Page/Page column 8
[3] Patent: US2015/105384, 2015, A1. Location in patent: Paragraph 0174; 0175
[4] Patent: WO2016/57779, 2016, A2. Location in patent: Page/Page column 63
[5] Patent: KR2017/43091, 2017, A. Location in patent: Paragraph 0693-0696

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