Triphosgene → 3-Oxo-2-phenyl-piperazine-1-carbonyl Chloride

HRID 1592785Notes

Reaction equation

HRID 1592785 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.[C:13]1([CH:19]2[NH:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[O:25]=[C:20]1[NH:21][CH2:22][CH2:23][N:24]([C:7]([Cl:10])=[O:6])[CH:19]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 2506813-Phenylpiperazin-2-one

Product 1

HCID 131904773-Oxo-2-phenyl-piperazine-1-carbonyl ChlorideYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of triphosgene (0.558 g) in DCM (10 ml) pyridine (0.46 mL) was added at 0° C. and, after 10 min, 3-phenyl-piperazine-2-one (1 g). The ice bath was removed and the mixture was stirred at room temperature overnight. The mixture was concentrated and the product was purified by flash chromatography (CH/AcOEt 1:1) to give the title compound (0.253 g) as a foam.

Workup

  1. customThe ice bath was removed
  2. concentrationThe mixture was concentrated
  3. customthe product was purified by flash chromatography (CH/AcOEt 1:1)

Sources & evidence

ORD record
ord-d46e3bd95d41497383eaff01878d3e34
Source dataset
uspto-grants-2007_11
Patent number
USRE039921E1

Reaction notes

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