N-[1-(2-Nitro-phenyl)-piperidin-4-yl]-acetamide → HCID 59794656, compound

HRID 32880Notes

Reaction equation

HRID 32880 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:11]1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:11][CH2:12][CH:13]([NH:16][C:17](=[O:19])[CH3:18])[CH2:14][CH2:15]1

Participants

4

Reactant 1

HCID 49431108N-[1-(2-Nitro-phenyl)-piperidin-4-yl]-acetamide

Product 1

HCID 59794656HCID 59794656, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[1-(2-nitro-phenyl)-piperidin-4-yl]-acetamide (as prepared in the previous step) (55 mg, 0.21 mmol) in methanol (10 mL) was added 10% palladium on carbon (50 mg) and the mixture stirred at RT for 1 h under hydrogen (1 atm). The mixture was filtered through a short column of Celite and the solvent removed in vacuo to yield 48 mg (100%) of the title compound as a purple solid. 1H-NMR (400 MHz, CDCl3): δ 6.82-6.67 (m, 4H), 4.44 (m, 1H), 3.78 (m, 1H), 3.35 (br s, 2H), 3.21 (m, 1H), 2.91 (m, 1H), 2.11 (s, 3H), 2.12-2.04 (m, 2H), 1.75 (br s, 1H), 1.41 (m, 2H). LC-MS (ESI, m/z): Calcd. for C13H20N3O, 234.2 (M+H); found: 234.0.

Workup

  1. filtrationThe mixture was filtered through a short column of Celite
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e36bc6484efd41578b0c3927a79b06f2
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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