Sodium borohydride → N-[2-[(5-Piperidinomethyl-2-furanyl)methylamino]ethyl]-2,3-dihydro-2-oxo-1H-benzimidazole

HRID 1461271Notes

Reaction equation

HRID 1461271 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].[N:14]1([CH2:20][C:21]2[O:27][C:24]([CH:25]=O)=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[BH4-].[Na+]>C(O)C>[N:14]1([CH2:20][C:21]2[O:27][C:24]([CH2:25][NH:1][CH2:2][CH2:3][N:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[NH:6][C:5]3=[O:13])=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 117451761-(2-aminoethyl)-2,3-dihydro-2-oxo-1H-benzimidazoleHCID 156753865-(Piperidin-1-ylmethyl)furan-2-carbaldehyde

Product 1

HCID 10450804N-[2-[(5-Piperidinomethyl-2-furanyl)methylamino]ethyl]-2,3-dihydro-2-oxo-1H-benzimidazoleYield 52.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 ml of dry ethanol were dissolved 1.2 g (6.78 mmol) of Compound j and 1.3 g (6.78 mmol) of 5-piperidinomethylfurfural and the solution was stirred at room temperature for 20 hours. The reaction mixture was then cooled with ice and 1.18 g (31.1 mmol) of sodium borohydride was gradually added. The mixture was further stirred under ice-cooling for 1.5 hours. The reaction mixture was then concentrated, and after addition of methylene chloride, the resulting solution was washed with 2 portions of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. Finally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1→chloroform-methanol-triethylamine=100:10:1) to give 1.26 g (52.9%) of Compound 18 as light yellow oil.

Workup

  1. additionwas gradually added
  2. stirringThe mixture was further stirred under ice-
  3. temperaturecooling for 1.5 hours
  4. concentrationThe reaction mixture was then concentrated
  5. additionafter addition of methylene chloride
  6. washthe resulting solution was washed with 2 portions of saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customFinally the residue was purified by silica gel column chromatography (chloroform-methanol=10:1→chloroform-methanol-triethylamine=100:10:1)

Sources & evidence

ORD record
ord-dfb4e838d16c4b598b337827b414810e
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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