Ammonia → HCID 54385985, compound

HRID 437635Notes

Reaction equation

HRID 437635 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[N+:26]([O-])=O)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.O1CCCC1.[H][H].N>[Ni].CO>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([NH:18][CH2:17][CH2:16][N:13]1[CH2:12][CH2:11][CH:10]([N:6]2[C:5]3[CH:30]=[CH:31][C:2]([Cl:1])=[CH:3][C:4]=3[NH:8][C:7]2=[O:9])[CH2:15][CH2:14]1)=[O:29]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 21428800HCID 21428800, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54385985HCID 54385985, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 16 parts of N{2-[4-(5-chloro-2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-nitrobenzamide in 90 parts of tetrahydrofuran and 40 parts of methanol is hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, there is added a solution of methanol, previously saturated with gaseous ammonia. The catalyst is filtered off and the filtrate is evaporated. The residue is taken up in acidified water and the whole is washed twice with trichloromethane. The aqueous phase is separated and alkalized with a diluted sodium hydroxide solution. The product is extracted twice with trichloromethane. The combined extracts are washed three times with water, dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and crystallized from a mixture of ethanol and a small amount of water, yielding 2 parts of 2-amino-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl} benzamide; mp. 226.8° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. washthe whole is washed twice with trichloromethane
  4. customThe aqueous phase is separated
  5. extractionThe product is extracted twice with trichloromethane
  6. washThe combined extracts are washed three times with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is triturated in 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customcrystallized from a mixture of ethanol

Sources & evidence

ORD record
ord-157b360f0712493bb122c8d0084c6480
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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