Hydrochloric Acid → Methyl-phenethyl-piperidin-4-YL-amine

HRID 962772Notes

Reaction equation

HRID 962772 reaction equation
Cl.[CH3:2][N:3]([CH:12]1[CH2:17][CH2:16][N:15](CC2C=CC=CC=2)[CH2:14][CH2:13]1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H][H]>C(O)C.O.[C].[Pd]>[CH3:2][N:3]([CH:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 13784444-[N-methyl-N-(2-phenylethyl)amino]-1-benzylpiperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 10856966Methyl-phenethyl-piperidin-4-YL-amineYield 70.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

60 ml of concentrated hydrochloric acid and 13.3 g of 10% palladium-carbon were added to a solution of 266 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-benzylpiperidine in 1 liter of ethanol and 500 ml of water. The mixture was stirred at a hydrogen pressure of 1 atm. at 60° C. for 5 hours. 10% palladium-carbon was removed by filtration and then washed with ethanol. The filtrate and the washings were combined and concentrated under reduced pressure. The residue was added to ice water. The mixture was made alkaline with a 25% aqueous sodium hydroxide solution and then extracted with methylene chloride. The extract was water-washed and then concentrated under reduced pressure. The residue was subjected to vacuum distillation to obtain 131.9 g of 4-[N-methyl-N-(2-phenylethyl)amino]piperidine as a colorless oil.

Workup

  1. custom10% palladium-carbon was removed by filtration
  2. washwashed with ethanol
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was added to ice water
  5. extractionextracted with methylene chloride
  6. washwashed
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-2fe0240dcca04678a6909ca923e31307
Source dataset
uspto-grants-1998_06
Patent number
US05760058

Reaction notes

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