Benzylamine → 1-(2-Phenylethyl)piperidin-4-amine

HRID 1979634Notes

Reaction equation

HRID 1979634 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([NH2:23])C1C=CC=CC=1>CO.S1C=CC=C1.[Pd]>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH2:23])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 7504BenzylamineHCID 96437N-Phenethyl-4-piperidinone

Product 1

HCID 107287881-(2-Phenylethyl)piperidin-4-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8030ThiopheneSolvent

Procedure

Following the procedure of Lobbezoo, J. Med. Chem. 24:777 (1981). N-(β-phenylethyl)-4-piperidinone (15.0 g, 74.0 mmol) dissolved in 200 ml of methanol containing 1 ml of a 4% thiophene in methanol solution is treated with benzyl amine (10.0 g, 93.0 mmol) and 2 g of 10% palladium-on-carbon in a Parr flask and hydrogenated for 18 hours (initial pressure, 26.5 psi, final pressure 22.0 psi). The catalyst is filtered and replaced with 2.0 g of fresh 10% palladium-on-carbon. The catalyst is filtered and replaced again with 4.8 g of fresh 10% palladium-on-carbon. The hydrogenation is followed over 3 days, at which point, hydrogen uptake ceases (initial pressure, 35 psi, final pressure, 29 psi). The catalyst is filtered through Celite and is washed with methanol. GLC analysis (2 ft SE-30, 100 C, 1 minute, programmed 20 C/minute rise to 250 C) indicated that 7% unreacted benzyl amine remained). This material nevertheless was used for subsequent experiments.

Workup

  1. filtrationThe catalyst is filtered
  2. filtrationThe catalyst is filtered
  3. filtrationThe catalyst is filtered through Celite
  4. washis washed with methanol
  5. customGLC analysis (2 ft SE-30, 100 C, 1 minute, programmed 20 C/minute rise to 250 C)

Sources & evidence

ORD record
ord-8efa98df0e7344a8b2a9a43ef490378a
Source dataset
uspto-grants-1984_11
Patent number
US04481360

Reaction notes

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