HCID 67143051, compound → HCID 67144123, compound

HRID 1454414Notes

Reaction equation

HRID 1454414 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[CH:10]=[C:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:4][CH2:3]1.[H][H]>[Pd].CO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[CH2:10][CH:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 67143051HCID 67143051, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67144123HCID 67144123, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-[2-(1-Methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-benzylidene]-pyrrolidin-2-one (Example 78), 308 mg, 1.15 mmol) and 10% palladium on carbon (300 mg) in methanol (20 mL) was placed under 50 psi hydrogen and was heated at 50° C. for 8 hours. The mixture was cooled to room temperature, was filtered through Celite™, and the solvent was removed in vacuo to afford 310 mg (99% yield) of the title compound. 13C NMR (100 MHz, CDCl3) d 180.1, 144.5, 136.8, 129.9, 127.1, 126.6, 126.2, 56.7, 46.7, 42.7, 40.6, 37.2, 33.9, 33.6, 33.5, 27.7; MS (AP/Cl) 273.2 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationwas filtered through Celite™
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7db54a8ca65e43beb15607fde8adad7a
Source dataset
uspto-grants-2009_01
Patent number
US07479559B2

Reaction notes

Loading…