HCID 21428883, compound → HCID 21428930, compound

HRID 437674Notes

Reaction equation

HRID 437674 reaction equation
[Cl:1][C:2]1[C:3]([N+:31]([O-])=O)=[CH:4][C:5]([O:29][CH3:30])=[C:6]([CH:28]=1)[C:7]([NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1)=[O:8].[H][H]>[Ni].C(O)(=O)C>[NH2:31][C:3]1[C:2]([Cl:1])=[CH:28][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:27])[CH2:16][CH2:17]2)=[O:8])=[C:5]([O:29][CH3:30])[CH:4]=1

Participants

5

Reactant 2

HCID 21428883HCID 21428883, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21428930HCID 21428930, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4.2 parts of 5-chloro-N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-2-methoxy-4-nitrobenzamide in 150 parts of acetic acid 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. Water is added to the residue and the whole is alkalized with a diluted sodium hydroxide solution. The precipitated product is filtered off and crystallized from methanol. The product is filtered off (the filtrate is set aside) and dried, yielding a first fraction of 0.8 parts of 4-amino-5-chloro-N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-2-methoxybenzamide; mp. 230.1° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. additionWater is added to the residue
  4. filtrationThe precipitated product is filtered off
  5. customcrystallized from methanol
  6. filtrationThe product is filtered off (the filtrate
  7. customdried

Sources & evidence

ORD record
ord-a2ed77ad2d3548109595715a1d2da7d4
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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