1-[(4-fluorophenyl)methyl]-N-[1'-(phenylmethyl)-[1,3'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine → 2-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazole

HRID 280335Notes

Reaction equation

HRID 280335 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18]C2CCN(C3CCCN(CC4C=CC=CC=4)C3)CC2)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH2:18])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 135880701-[(4-fluorophenyl)methyl]-N-[1'-(phenylmethyl)-[1,3'-bipiperidin]-4-yl]-1H-benzimidazol-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 30193052-amino-1-((4-fluorophenyl)methyl)-1H-benzimidazoleYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 11.3 parts of 1-[(4-fluorophenyl)methyl]-N-[1'-(phenylmethyl) -[1,3'-bipiperidin]-4-yl]-1H-benzimidazol-2-amine and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 8.5 parts (91.5%) of N-([1,3'-bipiteridin]-4-yl)-1-[(4-fluorophenylmethyl]-1H-benzimidazol-2-amine (57).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-2058c165145c4b94a83cb02e5796b0f6
Source dataset
uspto-grants-1986_05
Patent number
US04588722

Reaction notes

Loading…