Benzaldehyde → 3-(1H-Benzimidazol-1-yl)-N-benzylpropan-1-amine

HRID 1902459Notes

Reaction equation

HRID 1902459 reaction equation
[H][H].[N:3]1([CH2:12][CH2:13][CH2:14][NH2:15])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Pd].C(O)C>[CH2:16]([NH:15][CH2:14][CH2:13][CH2:12][N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 39208493-(1H-1,3-benzodiazol-1-yl)propan-1-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 204690543-(1H-Benzimidazol-1-yl)-N-benzylpropan-1-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

0.5 Gram of 10% palladium on charcoal was prehydrogenated in 100 ml. of absolute ethanol until the uptake of hydrogen stopped. Then, a solution of 10 grams of 1H-benzimidazole-1-propanamine and 6.7 grams of benzaldehyde in 50 ml. of absolute ethanol was added and the mixture was stirred at atmospheric pressure and room temperature under hydrogen until the calculated amount of hydrogen was taken up. The catalyst was then removed by filtration and the solvent was evaporated to leave N-benzyl-1H-benzimidazole-1-propanamine as a colorless oil. This material was sufficiently pure for further reaction but, if desired, a pure sample could be obtained by column chromatography on silica gel.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5ab23850e9a44aa79a3e87306aef8c55
Source dataset
uspto-grants-1982_12
Patent number
US04363808

Reaction notes

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