Propyl chloroformate → Piperazine-1,4-dicarboxylic acid propyl ester tert-butyl ester

HRID 1970554Notes

Reaction equation

[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:21]([O:24][C:25](Cl)=[O:26])[CH2:22][CH3:23]>ClCCl>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:25]([O:24][CH2:21][CH2:22][CH3:23])=[O:26])[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5.0 g tert-butyl 1-piperazinecarboxylate in 64 ml dichloromethane were added 8.2 ml triethylamine. The solution was cooled to 0° C. and 3.3 ml propylchloroformate were added dropwise at this temperature. After stirring for 12 h the reaction mixture was diluted with dichloromethane and washed with 0.1 M HCl and saturated NaHCO3. The crude product obtained after evaporation of the solvent was directly used in the next reaction step.

Workup

washwashed with 0.1 M HCl and saturated NaHCO3

Sources & evidence

ORD record: ord-d74ddf1eb2ed415eb8cddb232deea26e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426420B2

Reaction notes

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