Water → HCID 86695327, compound

HRID 2404482Notes

Reaction equation

HRID 2404482 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#N.[OH2:27]>C(O)=O.[Pt](=O)=O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)[C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:27]

Participants

5

Reactant 2

HCID 962WaterHCID 66836014HCID 66836014, compound

Product 1

HCID 86695327HCID 86695327, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 284Formic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]benzonitrile (example 172, 740 mg) in 80% aqueous formic acid (3 mL) is added platinum(IV) oxide (48 mg). The reaction mixture is heated at 60° C. for 7 h, then at room temperature for 2 days. As the reaction is not complete, 80% aqueous formic acid (3 mL) and platinum (IV) oxide (48 mg) are added and the reaction mixture is heated at 60° C. overnight. Water is added and the reaction mixture is filtered on celite. The phase is basified by adding a solution of 1N sodium hydroxide and extracted by ethyl acetate. The organic phase is washed by water, then dried over magnesium sulfate and concentrated to give 3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]benzaldehyde. 1H NMR: 9.99 (s, 1H), 9.67 (sl, 1H), 8.01 (s, 1H), 7.85-7.65 (m, 2H), 7.60-7.40 (m, 2H), 7.32-7.15 (m, 3H), 5.95 (s, 1H), 3.65-3.50 (m, 1H), 2.82-2.65 (m, 2H), 2.26 (s, 3H), 2.20-1.65 (m, 6H).

Workup

  1. temperaturethe reaction mixture is heated at 60° C. overnight
  2. filtrationthe reaction mixture is filtered on celite
  3. additionby adding a solution of 1N sodium hydroxide
  4. extractionextracted by ethyl acetate
  5. washThe organic phase is washed by water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-63fd421cfc514dc1acef16c0202f96fe
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

Loading…