HCID 69061372, compound → HCID 69069391, compound

HRID 1436877Notes

Reaction equation

HRID 1436877 reaction equation
[C:1]([C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[CH:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:5](=[O:17])[CH2:4]1)#[N:2].[H][H]>CO.[Pd]>[C:1]([C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:5](=[O:17])[CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 69061372HCID 69061372, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69069391HCID 69069391, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 4-cyano-1-(4-fluorobenzyl)-4-phenyl-1,2,3,4-tetrahydropyridin-2-one (3.98 g, 13.0 mmol) in degassed methanol was added 10% Pd/C (0.8 g). The reaction shaken under an atmosphere of 33 psi of hydrogen for 18 hours. More 10% Pd/C (0.4 g) was added and the mixture was shaken under 45 psi of hydrogen for 48 hours. The mixture was filtered through a bed of celite and the filtrate was concentrated to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.55 (d, J=7.7 Hz, 2H), 7.46 (t, J=7.9 Hz, 2H), 7.38 (t, J=7.3 Hz, 1H), 7.28 (t, J=3 Hz, 2H), 7.16 (t, J=2.4 Hz, 2H), 4.58 (s, 2H), 3.44 (m, 1H), 3.25 (m, 1H), 3.07 (q, J=16 Hz, 2H), 2.41 (s, 2H) ppm. ES MS M+1=309.

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d07abb945e984b74a430b560cc4d8fa8
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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