Triethylamine → 4-(Bis(4-chlorophenyl)methyl)piperazin-2-one

HRID 494052

Reaction equation

HRID 494052 reaction equation
Cl[CH:2]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][C:18]1=[O:23].C(N(CC)CC)C>CC#N>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:20]2[CH2:21][CH2:22][NH:17][C:18](=[O:23])[CH2:19]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130784,4'-Dichlorobenzhydryl chlorideHCID 231360Piperazin-2-one

Product 1

HCID 689317794-(Bis(4-chlorophenyl)methyl)piperazin-2-oneYield 83.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of chlorobis(4-chlorophenyl)methane (407 mg, 1.5 mmol) in MeCN was added piperazin-2-one (601 mg, 6.0 mmol) followed by triethylamine (626 μl, 4.5 mmol) and the resulting mixture was refluxed overnight. After cooling to rt, the solvent was evaporated to dryness and the residue was submitted to column chromatography (SiO2, DCM to DCM/MeOH=100:5) to give 4-(bis(4-chlorophenyl)methyl)piperazin-2-one (420 mg) as a white solid.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-27f77bb0ef1241de99bd80c85f018621
Source dataset
uspto-grants-2009_05
Patent number
US07538114B2

Linked notes

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