HCID 20482634, compound → HCID 21493460, compound

HRID 2064202Notes

Reaction equation

HRID 2064202 reaction equation
[CH3:1][C:2]1[C:24]([CH3:25])=[CH:23][C:5]2[N:6]([C:10]3[CH2:11][CH2:12][N:13](CC4C=CC=CC=4)[CH2:14][CH:15]=3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[H][H]>C(O)C.C(O)(=O)C.[Pd]>[CH3:1][C:2]1[C:24]([CH3:25])=[CH:23][C:5]2[N:6]([C:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH:15]=3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 20482634HCID 20482634, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21493460HCID 21493460, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 5,6-dimethyl-1-[1-(phenylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1,3-dihydro-2H-benzimidazol-2-one (D99) (1.05 mmol, 350 mg) in ethanol (10 mL) and acetic acid (2 mL) was treated with 10% palladium on charcoal (0.25 eq wt, 90 mg) then shaken under 50 PSI of hydrogen pressure for 24 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give the acetate salt of the title compound also containing some saturated analogue (reduction of the C═C double bond in the piperidine core) as a beige solid (1.2 mmol, 370 mg, >100% yield) M+H 246.2, M−H 242.3.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9bc5766128dc4ebe92548269e9d7386f
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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