Methanol → HCID 68119151, compound

HRID 437675Notes

Reaction equation

HRID 437675 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:16](=[O:26])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)[CH2:9][CH2:8]2)[C:5]2[CH:27]=[CH:28][CH:29]=[CH:30][C:4]=2[NH:3]1.CO.[H][H]>[Ni].O1CCCC1>[OH2:1].[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][CH:7]([N:6]2[C:5]3[CH:27]=[CH:28][CH:29]=[CH:30][C:4]=3[NH:3][C:2]2=[O:1])[CH2:8][CH2:9]1)=[O:26].[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][CH:7]([N:6]2[C:5]3[CH:27]=[CH:28][CH:29]=[CH:30][C:4]=3[NH:3][C:2]2=[O:1])[CH2:8][CH2:9]1)=[O:26]

Participants

6

Reactant 3

HCID 887MethanolHCID 21428804HCID 21428804, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68119151HCID 68119151, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.5 parts of N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-2-nitrobenzamide, 80 parts of methanol and 45 parts of tetrahydrofuran 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 twice from 2-propanol. The product is filtered off and dried, yielding 2 parts of 2-amino-N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}benzamide hemihydrate; mp. 219.2° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized twice from 2-propanol
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-a3f818f5897b4cf49a0ff0bd917040df
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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