N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}-4-fluoro-2-nitrobenzamide → 2-amino-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1yl)-1-piperidinyl]ethyl}-4-fluorobenzamide hydrochloride dihydrate

HRID 437677Notes

Reaction equation

HRID 437677 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:18][C:19](=[O:30])[C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=4[N+:27]([O-])=O)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[H][H]>[Ni].CO>[OH2:9].[OH2:9].[ClH:1].[NH2:27][C:21]1[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:20]=1[C:19]([NH:18][CH2:17][CH2:16][N:13]1[CH2:14][CH2:15][CH:10]([N:6]2[C:5]3[CH:31]=[CH:32][C:2]([Cl:1])=[CH:3][C:4]=3[NH:8][C:7]2=[O:9])[CH2:11][CH2:12]1)=[O:30]

Participants

5

Reactant 2

HCID 21428824N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}-4-fluoro-2-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 214288462-amino-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1yl)-1-piperidinyl]ethyl}-4-fluorobenzamide hydrochloride dihydrate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.9 parts of N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1yl)-1-piperidinyl]ethyl}-4-fluoro-2-nitrobenzamide in 80 parts of methanol is hydrogenated at normal pressure and at room temperature with 1 part of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is converted into the hydrochloride salt in 4-methyl-2-pentanone and 2-propanol. The salt is filtered off and crystallized from a mixture of 2-propanone and water, yielding 0.2 parts of 2-amino-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1yl)-1-piperidinyl]ethyl}-4-fluorobenzamide hydrochloride dihydrate; mp. 250° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. filtrationThe salt is filtered off
  4. customcrystallized from a mixture of 2-propanone and water

Sources & evidence

ORD record
ord-26ed6c2eaf97481c92791b07a5c3d575
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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