Piperazine → HCID 14903418, compound

HRID 477041Notes

Reaction equation

HRID 477041 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1CCNCC1.C(=O)([O-])[O-].[K+].[K+].Br[CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O.CN(C=O)C>[CH:29]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][OH:15])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 14903424HCID 14903424, compound

Product 1

HCID 14903418HCID 14903418, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of (1) (the piperazine compound) (5.996 g, 29.1 mmol) was put in a 100 ml-three-necked flask, which was equipped with a Dimroth condenser on the central mouth and septum rubbers on the side mouths. In the flask, DMF (33 ml) was added to dissolve the content, and potassium carbonate (8.034 g, 58.1 mmol) and bromodiphenylmethane (7.543 g, 30.5 mmol) were added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was added to water (80 ml) in a 200 ml-conical flask, and the mixture was extracted with diethyl ether (four times, 100 ml each time). The ether layer was washed with brine (twice, 40 ml each time), dried and distilled off under reduced pressure. The residue (10.616 g) was subjected to column chromatography [silica gel, ethyl acetate-n-hexane (1:1)] for separation and purification to give 6.188 g of the above-captioned benzhydrylpiperazine compound (Yield: 57%).

Workup

  1. customwas equipped with a Dimroth condenser on the central mouth and septum rubbers on the side mouths
  2. additionwere added
  3. extractionthe mixture was extracted with diethyl ether (four times, 100 ml each time)
  4. washThe ether layer was washed with brine (twice, 40 ml each time),
  5. customdried
  6. distillationdistilled off under reduced pressure
  7. customThe residue (10.616 g) was subjected to column chromatography [silica gel, ethyl acetate-n-hexane (1:1)] for separation and purification

Sources & evidence

ORD record
ord-80f15a1081a34e309579f0e9956d199e
Source dataset
uspto-grants-1989_12
Patent number
US04886819

Reaction notes

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