HCID 69068115, compound → 4-(1-Aminopropyl)-1-(4-fluorobenzyl)piperidin-2-one

HRID 1436881Notes

Reaction equation

HRID 1436881 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH:13]([N+:16]([O-])=O)[CH2:14][CH3:15])[CH2:9][C:8]2=[O:19])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni].O>[NH2:16][CH:13]([CH:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=2)[C:8](=[O:19])[CH2:9]1)[CH2:14][CH3:15]

Participants

6

Reactant 2

HCID 69068115HCID 69068115, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 690684334-(1-Aminopropyl)-1-(4-fluorobenzyl)piperidin-2-one

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-4-(1-nitropropyl)piperidin-2-one (2.8 g, 9.51 mmol) in ethanol (50 mL) was added Raney Nickel (2 grams of a 50% by weight slurry in water). The reaction mixture was shaken under 55 psi of hydrogen. After 24 hours, the reaction mixture was filtered through a bed a celite, then concentrated under vacuum to afford the title compound as a mixture of diastereomers. The first diastereomer has a retention time of 2.05 min and the second diastereomer has a retention time of 2.10 min. The HPLC method was performed on a Hewlett-Packard Zorbax SB-C8 column (75×4.6 mm, 3.5 micron) eluting with 5%-100% CH3CN (0.1% TFA) in H2O (0.1% TFA). ES MS M+1=265.

Workup

  1. filtrationthe reaction mixture was filtered through a bed a celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-df9d9f606bb64ef1b731e4f86b1fdefd
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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