HCID 21428811, compound → HCID 21428835, compound

HRID 437634Notes

Reaction equation

HRID 437634 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)=[O:7])=[C:4]([N+:29]([O-])=O)[CH:3]=1.[H][H]>[Ni].CO>[NH2:29][C:4]1[CH:3]=[C:2]([F:1])[CH:28]=[CH:27][C:5]=1[C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[NH:19][C:18]2=[O:26])[CH2:15][CH2:16]1)=[O:7]

Participants

5

Reactant 2

HCID 21428811HCID 21428811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21428835HCID 21428835, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8.7 parts of 4-fluoro-N-{2-[4-(2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-nitrobenzamide and 120 parts of methanol is hydrogenated at normal pressure and at room temperature with 2 parts 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 crystallized from a mixture of methanol and 2-propanol. The product is filtered off and dried, yielding 4.5 parts of 2-amino-N-{2-[4-(2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-4-fluorobenzamide; mp. 229.3° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized from a mixture of methanol and 2-propanol
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-d0043691558d4c94a999b4eb260d8707
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

Loading…