Acetic Acid → HCID 58998518, compound

HRID 1592998Notes

Reaction equation

HRID 1592998 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[CH3:26][S:23]([C:21]1[CH:20]=[CH:19][C:18]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:15]=[N:16][C:17]=2[CH:22]=1)(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 687092041-(1-benzylpiperidin-4-yl)-5-methylsulphonyl-1H-benzimidazole

Product 1

HCID 58998518HCID 58998518, compoundYield 793.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The crude material from step 3 (10 g) was dissolved in 1 litre of methanol in a pressure vessel, 20 g of moist 10% Pd/C catalyst and 100 mL acetic acid were added and stirred under an atmosphere of hydrogen at 5 bar and 50° C. for 8 hours. The reaction was cooled, filtered and evaporated. The residue was dissolved in water and basified with sodium hydroxide solution, extracted into dichloromethane, dried and evaporated. The brown solid was triturated with isopropanol, filtered, and washed with ether to give the title compound (60 g) as a pale grey solid; NMR: 2.00(m, 4H), 2.75(m, 2H), 3.15(m, 2H), 3.20(s, 3H), 4.60(m, 1H), 7.78 (dd, 1H), 7.85(d, 1H), 8.20(d, 1H), 8.56(s, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted into dichloromethane
  6. customdried
  7. customevaporated
  8. customThe brown solid was triturated with isopropanol
  9. filtrationfiltered
  10. washwashed with ether

Sources & evidence

ORD record
ord-80071eab113847ed91e78c28a618e3aa
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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