Phenyl isocyanate → Tert-butyl 4-phenylcarbamoyl-1-piperazinecarboxylate

HRID 1982796Notes

Reaction equation

HRID 1982796 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:21](=[O:22])[NH:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 20674603Tert-butyl 4-phenylcarbamoyl-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. solution of piperazine-1-carboxylic acid tert-butyl ester (114 g) in DCM (500 mL) was treated with phenyl isocyanate (65 mL). After 1 hour (h), the mixture was allowed to warm to room temperature (rt). After 15 h, the resulting mixture was filtered and the solid was washed with DCM (2×100 mL), giving the title compound as a white amorphous solid (95 g).

Workup

  1. waitAfter 15 h
  2. filtrationthe resulting mixture was filtered
  3. washthe solid was washed with DCM (2×100 mL)

Sources & evidence

ORD record
ord-f0c45d629bd2427cb7ec58477ec0b9d1
Source dataset
uspto-grants-2009_06
Patent number
US07541359B2

Reaction notes

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