Ammonia → HCID 15037481, compound

HRID 1886415Notes

Reaction equation

HRID 1886415 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][CH:18]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]#[N:25])[CH2:19]1.N.[H][H]>[Ni].CO>[NH2:25][CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][CH:18]([NH:17][C:9]2[N:8]([CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH2:19]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 15037525HCID 15037525, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15037481HCID 15037481, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 11 parts of 3-[[1-(2-pyridinylmethyl)-1H-benzimidazol-2-yl]amino]-1-pyrrolidineacetonitrile and 320 parts of methanol, saturated with ammonia was hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was solidified in 2,2'-oxybispropane while stirring. The product was filtered off and dried, yielding 10 parts (91%) of N-[1-(2-aminoethyl)-3-pyrrolidinyl]-1-(2-pyridinylmethyl)-1H-benzimidazol-2-amine; mp. 130° C. (compound 138).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-c6aa1ad5c5934e03880423d2105e6e8c
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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