Sodium borohydride → 1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidin-4-ol

HRID 2047381

Reaction equation

HRID 2047381 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([N:17]2[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[CH:13]=[CH:14][C:15]=1[Cl:16].[BH4-].[Na+]>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([N:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]2)[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 595682431-[3-(1H-benzo[d]imidazol-2-yl)-4-chlorophenyl]piperidin-4-one

Product 1

HCID 595683691-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidin-4-olYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-[3-(1H-benzoimidazol-2-yl)-4-chloro-phenyl]-piperidin-4-one (0.05 g, 0.17 mmol) in methanol (50 mL) was added sodium borohydride (NaBH4) (0.01 g, 0.17 mmol) and the resulting mixture was stirred for 1 h at room temperature and then quenched with few drops of water. The solvent was removed under reduced pressure, the crude dissolved in EtOAc (5 mL) and filtered, then the organic phase was evaporated under reduced pressure to afford 0.02 g (36%) of the title compound.

Workup

  1. customquenched with few drops of water
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe crude dissolved in EtOAc (5 mL)
  4. filtrationfiltered
  5. customthe organic phase was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b68508f9a2104c64b457a0df3cd08835
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Linked notes

Loading…