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

HRID 1926683Notes

Reaction equation

HRID 1926683 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-5ce8f1ae0940429681714c9903f674f9
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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