1-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one → 4-(1-Amino-1-methylethyl)-1-(4-fluorobenzyl)piperidine-2-one

HRID 1436870Notes

Reaction equation

HRID 1436870 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([C:13]([CH3:18])([N+:15]([O-])=O)[CH3:14])[CH2:9][C:8]2=[O:19])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni].O>[NH2:15][C: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)([CH3:18])[CH3:14]

Participants

6

Reactant 2

HCID 690609141-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 690668314-(1-Amino-1-methylethyl)-1-(4-fluorobenzyl)piperidine-2-one

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one (1.05 g, 3.57 mmol) in degassed ethanol (75 mL) was added Raney Nickel (2 g of a 50% by weight slurry in water). The reaction mixture was shaken under 55 psi of hydrogen fro 4 hours. The reaction mixture was filtered through a bed a celite, then concentrated under vacuum to give an oil that solidified on standing. The solid was triturated in ether and collected by filtration to give the title compound. 1H NMR (400 MHz, CDCl3) δ 7.22 (m, 2H), 7.02 (t, J=8.6 Hz, 2H), 4.65 (d, J=14.5 Hz, 1H), 4.44 (d, J=14.6 Hz, 1H), 3.26 (m, 2H), 2.60 (d, J=5 Hz, 1H), 2.25 (m, 1H), 1.97 (d, J=11.5 Hz, 1H), 1.75 (m, 1H), 1.44 (m, 1H), 1.11 (d, J=9 Hz, 6H) ppm. ES MS M+1=265.

Workup

  1. filtrationThe reaction mixture was filtered through a bed a celite
  2. concentrationconcentrated under vacuum
  3. customto give an oil that
  4. customThe solid was triturated in ether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e3a1fcdcfd5a4bde82e9fe2cbdd552d8
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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