2,6-Dimethylbenzaldehyde → 1-[1-[1-(2,6-Dimethylbenzyl)piperidin-4-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1179331Notes

Reaction equation

HRID 1179331 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[CH3:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:25]=1[CH:26]=O>CO.[Cl-].[Cl-].[Zn+2].[BH3-]C#N.[Na+]>[CH3:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:25]=1[CH2:26][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])[CH2:11][CH2:12]2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 5838412,6-DimethylbenzaldehydeHCID 15839552HCID 15839552, compound

Product 1

HCID 100476471-[1-[1-(2,6-Dimethylbenzyl)piperidin-4-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 2

HCID 131717307ZINC chloride sodium cyanoborohydrideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 19.8 mg of 1-[1-(piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one and 7.5 microliter of 2,6-dimethylbenzaldehyde in 1 ml of MeOH was added 274 microliter of 0.3M MeOH solution of ZnCl2—NaBH3CN at room temperature. The reaction mixture was stirred at room temperature for 2 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 the residue was purified with PNLC (CHCl3/MeOH/28% aqueous NH3=100/10/1) gave 11.8 mg of the target compound as a colorless solid.

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. customthe residue was purified with PNLC (CHCl3/MeOH/28% aqueous NH3=100/10/1)

Sources & evidence

ORD record
ord-a35a0de7f8cb447883c2552c74836de5
Source dataset
uspto-grants-2007_10
Patent number
US07279490B2

Reaction notes

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