Hydrochloric Acid → Benzhydrylpiperazine

HRID 1885880Notes

Reaction equation

HRID 1885880 reaction equation
C([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=O.Cl[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(O)C>[C:11]1([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]2[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7035ChlorodiphenylmethaneHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 70048Benzhydrylpiperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.2 g (98 mmoles) of 1-formylpiperazine was added to 10 g (49 mmoles) of chlorodiphenylmethane, and the solution was stirred at room temperature for 48 hours, and the mixture was extracted with water and methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and 8.9 g (31.9 mmoles) of the resulting formyl compound was dissolved in 100 ml of ethanol, and 6.5 g (64 mmoles) of conc. hydrochloric acid was added, and the solution was refluxed for 1 hour. Then, the solvent was evaporated under reduced pressure, and the residue was extracted with K2CO3 /water/CH2C2. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 6.8 9 (yield 55 %) of the desired product.

Workup

  1. extractionthe mixture was extracted with water and methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. temperaturethe solution was refluxed for 1 hour
  5. customThen, the solvent was evaporated under reduced pressure
  6. extractionthe residue was extracted with K2CO3 /water/CH2C2
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-43742df8c6f041b2b1461c918c520c60
Source dataset
uspto-grants-1992_09
Patent number
US05147876

Reaction notes

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