Potassium Carbonate → Tert-butyl 4-benzhydrylpiperazine-1-carboxylate

HRID 1457606Notes

Reaction equation

HRID 1457606 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].Br[CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 236603Bromodiphenylmethane

Product 1

HCID 4935532Tert-butyl 4-benzhydrylpiperazine-1-carboxylateYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.7 g of N-(tert-butoxycarbonyl)piperazine, 2.5 g of bromodiphenylmethane, 6.9 g of potassium carbonate and 20 ml of hexamethylphosphoramide was stirred at 40° to 50° C. for 4 hours. After cooling, water was added and the reaction mixture was extracted with diethyl ether. The exact was washed and dried, and the solvent was removed under reduced pressure. Hexane was added to the precipitated crystals and the crystals were collected by filtration to give 2.5 g of 4-(tert-butoxycarbonyl)-1-diphenylmethylpiperazine (melting point: 129°-131° C.).

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction mixture was extracted with diethyl ether
  3. washThe exact was washed
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. additionHexane was added to the precipitated crystals
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-07f4804c63e542a694dcb1c822559c1c
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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