Ammonium formate → 1-(4-Piperidinyl)-1H-benzimidazole

HRID 1068154Notes

Reaction equation

HRID 1068154 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 30197461-(1-(phenylmethyl)-4-piperidinyl)-1H-benzimidazole

Product 1

HCID 30192621-(4-Piperidinyl)-1H-benzimidazoleYield 118.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 196 mg of 1-(1-benzyl-piperidin-4-yl)-1-H-benzoimidazole (from Step B) in 10 mL of CH3OH was added 200 mg 10% palladium on carbon and 200 mg ammonium formate. After the reaction was refluxed for 4 hours, the mixture was cooled down to room temperature, filtered through Celite and washed with CH3OH. The filtrate was concentrated under reduced pressure to give 160 mg of the title compound as oil. 1H NMR (400 MHz, CD3OD): δ2.13(m, 4H), 2.92(m, 2H), 3.27(m, 2H), 4.56(m, 1H), 7.28(m, 2H), 7.66(t, J=5.9 Hz, 2H), 8.25(s, 1H). ESI-MS 201 (M+H); HPLC A: 0.61 min.

Workup

  1. temperatureAfter the reaction was refluxed for 4 hours
  2. filtrationfiltered through Celite
  3. washwashed with CH3OH
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aba91a94bac1458da079612a5b087eac
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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