HCID 59737058, compound → 1-[(Piperidin-3-yl)methyl]pyridin-2(1H)-one

HRID 1660723Notes

Reaction equation

HRID 1660723 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]2=[O:24])[CH2:12]1)=O)C1C=CC=CC=1>CCO.[Pd]>[NH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]2=[O:24])[CH2:12]1

Participants

4

Reactant 1

HCID 59737058HCID 59737058, compound

Product 1

HCID 444105331-[(Piperidin-3-yl)methyl]pyridin-2(1H)-oneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2-oxo-2H-pyridin-1-ylmethyl)piperidine-1-carboxylic acid benzyl ester (100 mg) and 5% Pd—C (20 mg) in EtOH (15 mL) was stirred under H2 (1 atm). The reaction was traced by TLC. The catalyst was filtered and the filtration was concentrated and purified by chromatography with CH2Cl2-MeOH—NH3.H2O (10:1:0.1) to give a syrup (50 mg, 85%). 1H NMR (CDCl3) δ 7.31 (m, 1H), 7.21 (dd, 1H, J=6.9, 2.1 Hz), 6.56 (d, 1H, J=9.0 Hz), 6.14 (td, 1H, J=6.6, 1.5 Hz), 3.90 (dd, 1H, J=13.0, 8.1 Hz) 3.76 (dd, 1H, J=13.0, 6.7 Hz), 2.98 (m, 2H), 2.62 (t, 1H, J=9.8 Hz), 2.44 (t, 1H, J=11.2 Hz), 2.10-1.10 (m, 6H).

Workup

  1. filtrationThe catalyst was filtered
  2. filtrationthe filtration
  3. concentrationwas concentrated
  4. custompurified by chromatography with CH2Cl2-MeOH—NH3.H2O (10:1:0.1)

Sources & evidence

ORD record
ord-9fb9615441cc4fd0b91670ef5dd1348e
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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