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

HRID 1970652Notes

Reaction equation

[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:24]([O:27][C:28](Cl)=[O:29])[CH2:25][CH3:26]>ClCCl>[CH2:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:28]([O:27][CH2:24][CH2:25][CH3:26])=[O:29])[CH2:3][CH2:2]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 15.0 g benzyl 1-piperazinecarboxylate in 100 ml dichloromethane were added 20.7 ml triethylamine. The solution was cooled to 0° C. and 8.4 ml propylchloroformate added dropwise at this temperature. After stirring for 1 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 purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 19.3 g.

Workup

washwashed with 0.1 M HCl and saturated NaHCO3

Sources & evidence

ORD record: ord-e8fc38689c1442ef83ead0f1f5adddbb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426420B2

Reaction notes

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