Phenethylamine → HCID 1378357, compound

HRID 369172Notes

Reaction equation

HRID 369172 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:18]1([CH2:21][CH2:22][NH:23][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:4][CH2:3]2)[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 192201-Benzyl-4-piperidone

Product 1

HCID 1378357HCID 1378357, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

2 g of p-toluenesulfonic acid was added to a solution of 230 g of 4-oxo-1-benzylpiperidine and 221 g of 2-phenethylamine in 1 liter of toluene. The mixture was refluxed for 1 hour while removing the generated water using a Dean-Stark trap. The reaction mixture was concentrated under reduced pressure. To the residue was added 1 liter of ethanol. To the mixture being ice-cooled was slowly added 22 g of sodium boron hydride. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was ice-cooled, and then was made acidic by slow addition of concentrated hydrochloric acid. The resulting crystals were collected by filtration. The crystals were dissolved in water. The solution was made alkaline with a 25% aqueous sodium hydroxide solution and then extracted with methylene chloride. The extract was water-washed, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 222.2 g of 4-(2-phenylethylamino)-1-benzylpiperidine as a light yellow oily substance.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customwhile removing the generated water using a Dean-Stark trap
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue was added 1 liter of ethanol
  5. temperaturecooled
  6. temperaturecooled
  7. additionwas made acidic by slow addition of concentrated hydrochloric acid
  8. filtrationThe resulting crystals were collected by filtration
  9. dissolutionThe crystals were dissolved in water
  10. extractionextracted with methylene chloride
  11. washwashed
  12. dry with materialdried with anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8de577f70b74a98bfb78d367e4fd281
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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