Hydrochloric Acid → 4-(Diphenylmethyl)piperidine hydrochloride

HRID 2297513Notes

Reaction equation

HRID 2297513 reaction equation
[ClH:1].[C:2]1([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[H][H]>[C].[Pd].CO>[ClH:1].[C:2]1([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 135045484-Diphenylmethylenepiperidine hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 230040934-(Diphenylmethyl)piperidine hydrochlorideYield 38.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-diphenylmethylenepiperidine hydrochloride (6.21 g) was added to methanol (30 ml) and the atmosphere was replaced with argon. To the mixture, 10% palladium-carbon (1.54 g) and a small amount,of concentrated hydrochloric acid were added and the atmosphere was replaced with hydrogen, followed by allowing the mixture to react at 3.5 atm at room temperature for 10.5 hours. Then 10% palladium-carbon was removed through Celite and the filtrate was concentrated. The residue was again dissolved in methanol (30 ml) and 10% palladium-carbon (10 g) and a small amount of hydrochloric acid were added. The atmosphere was replaced with hydrogen, and the mixture was allowed to react at 3.5 atm at room temperature for 21 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated, followed by recrystallizing the residue from methanol/ether to obtain 2.38g of 4-diphenylmethylpiperidine hydrochloride. Yield: 38%.

Workup

  1. customto react at 3.5 atm at room temperature for 10.5 hours
  2. customThen 10% palladium-carbon was removed through Celite
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was again dissolved in methanol (30 ml)
  5. addition10% palladium-carbon (10 g) and a small amount of hydrochloric acid were added
  6. customto react at 3.5 atm at room temperature for 21 hours
  7. filtrationThe reaction mixture was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customby recrystallizing the residue from methanol/ether

Sources & evidence

ORD record
ord-26dd78430b7e40fcbf63646fbe236b18
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

Loading…