Water → Piperazine-1,4-dicarboxylic acid tert-butyl ester phenyl ester

HRID 1970550Notes

Reaction equation

HRID 1970550 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.[C:21]1([O:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>ClCCl>[C:21]1([O:27][C:28]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11529616Piperazine-1,4-dicarboxylic acid tert-butyl ester phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g tert-butyl 1-piperazinecarboxylate and 1.5 ml triethylamine in 5 ml dichloromethane were added at 0° C. 0.8 ml phenylchloroformate. After stirring for 12 h, 2 ml of water were added and the mixture loaded on a chem Elute® cartridge. Elution with dichloromethane yielded the crude product which was used in the subsequent reaction.

Workup

  1. washElute® cartridge
  2. washElution with dichloromethane

Sources & evidence

ORD record
ord-3d6fb343e9ea454ea03aa22599840fb7
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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