4-Nitrophenyl chloroformate → HCID 22462238, compound

HRID 2353109Notes

Reaction equation

HRID 2353109 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:16]>C(Cl)Cl.C(N(CC)CC)C>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][C:15]([N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)=[O:16])=[CH:23][CH:22]=1)([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22462238HCID 22462238, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Amine preparation: to N-BOC-piperazine (500 mg) in DCM (5 mL) and triethylamine (0.41 ml) was added 4-nitrophenyl chloroformate (541 mg). After 1 h the reaction mixture was diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo to yield piperazine-1,4-dicarboxylic acid tert-butyl ester 4-nitro-phenyl ester (940 mg).

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e670f52906944f16ad933fe2822ab144
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

Loading…