1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → Tbpb

HRID 1179330Notes

Reaction equation

HRID 1179330 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.[CH3:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>CO.[Cl-].[Cl-].[Zn+2].[BH3-]C#N.[Na+]>[CH3:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[CH2:20][N:21]1[CH2:22][CH2:23][CH:24]([N:10]2[CH2:9][CH2:8][CH:7]([N:6]3[C:5]4[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=4[NH:3][C:2]3=[O:1])[CH2:12][CH2:11]2)[CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 11959536N-(2-methylbenzyl)4-piperidone

Product 1

HCID 10092649TbpbYield 58.1%

Reagents, catalysts & solvents 2

HCID 131717307ZINC chloride sodium cyanoborohydrideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.73 g of 4-(2-keto-1-benzimidazolyl)piperidine and 1.54 g of N-(2-methylbenzyl)4-piperidone in 20 ml of MeOH was added 51 ml of 0.3M methanolic solution of ZnCl2—NaBH3CN at room temperature. The reaction mixture was stirred at room temperature for 4 h and quenched with saturated aqueous NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with the 1:1 solution of saturated aqueous NaHCO3 and brine, and dried over anhydrous Na2SO4. The organic solvent was evaporated and recrystallization of the residue from EtOAc gave 1.78 g of the target compound as a colorless powder.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with the 1:1 solution of saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe organic solvent was evaporated
  6. customrecrystallization of the residue from EtOAc

Sources & evidence

ORD record
ord-40c9988a9dc94a52a8feb15dcc080e05
Source dataset
uspto-grants-2007_10
Patent number
US07279490B2

Reaction notes

Loading…