Ammonia → 4-(1H-Benzo[d]imidazol-1-yl)butan-2-amine

HRID 1981176Notes

Reaction equation

HRID 1981176 reaction equation
[N:1]1([CH2:10][CH2:11][C:12](=O)[CH3:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH3:15]>[Ni].C(OCC)(=O)C>[NH2:15][CH:12]([CH3:13])[CH2:11][CH2:10][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 132678772-Butanone, 4-(1H-benzimidazol-1-yl)-

Product 1

HCID 132678794-(1H-Benzo[d]imidazol-1-yl)butan-2-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzimidazole (VIII) (1 mole), condensed with methylvinylketone in slight excess (1-1.1 mole), in the presence of a catalytic amount of Triton B (benzyltrimethylammonium hydroxide), gives 1-[1-benzimidazolyl]-3-oxo butane (IX). This reaction is conducted in a non-polar neutral solvent, such as an aromatic hydrocarbon (for example toluene) or, preferably, ethyl acetate. The ketone (IX) is converted, by known process, into its oxime ((X). The latter, by catalytic hydrogenation, in an alcoholic medium, in the presence of ammonia and Raney nickel, under pressure (20-80 bars) and heat (50° to 100° C.), results in the amine (III). ##STR6##

Sources & evidence

ORD record
ord-787619b8e1c44b13849777d24ab978b9
Source dataset
uspto-grants-1985_04
Patent number
US04513001

Reaction notes

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