HCID 11074826, compound → 3-phenylpiperidin-2-one

HRID 1667174Notes

Reaction equation

HRID 1667174 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](OCC)=[O:7])#[N:2]>N.CO.[Ni]>[C:11]1([CH:5]2[CH2:4][CH2:3][CH2:1][NH:2][C:6]2=[O:7])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 11074826HCID 11074826, compound

Product 1

HCID 117897263-phenylpiperidin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A solution of the product from Example 91A (2.42 g, 11.14 mmol) in 7 M ammonia/methanol (40 mL) was added to solvent washed Raney®-nickel (24.20 g, 412 mmol) in a 250 mL stainless steel pressure bottle and stirred for 16 hours under hydrogen at 30 pounds per square inch at room temperature. The mixture was filtered through a nylon membrane and concentrated to supply the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.39-7.17 (m, 5H), 6.00 (s, 1H), 3.65 (dd, J=6.2, 8.3, 1H), 3.54-3.32 (m, 2H), 2.33-2.10 (m, 1H), 2.06-1.70 (m, 3H); MS (ESI+) m/z 176.1 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated to supply the title compound

Sources & evidence

ORD record
ord-9d432e48c0e3459895cbba9f2a3dc6c2
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…