Dichloromethane → 1-(4-Amino-phenyl)-piperidin-4-one hydrochloride

HRID 1794847Notes

Reaction equation

HRID 1794847 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(Cl)[Cl:18]>[Pd]>[ClH:18].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][C:13](=[O:16])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 38425621-(4-Nitrophenyl)piperidin-4-one

Product 1

HCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1-(4-nitro-phenyl)-piperidin-4-one (Synthesis 1981, 606) (4.0 g, 18 mmol) and 500 mg of 10% Pd/C in 75 mL of methylene chloride was hydrogenated under H2 (5˜10 psi) for 1 hour. The catalyst was then removed by filtering through a short pad of silica gel. The filtrate was treated with hydrogen chloride gas and the precipitate was collected to give 2 g of the title compound as a tan solid; 1H NMR (300 MHz, DMSO-d6) δ 2.44 (t, J=6.0 Hz, 4 H), 3.65 (t, J=6.0 Hz, 4 H), 7.14 (d, J=9.0 Hz, 2 H), 7.25 (d, J=9.0 Hz, 2 H); MS (ES) m/z: 190.9 (MH+); HRMS Calcd. for C11H15N2O (MH+): 190.1106. Found: 190.1096.

Workup

  1. customThe catalyst was then removed
  2. filtrationby filtering through a short pad of silica gel
  3. additionThe filtrate was treated with hydrogen chloride gas
  4. customthe precipitate was collected

Sources & evidence

ORD record
ord-9a3713294a5a43b98d04ed7f69e02f5d
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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