Ammonia → 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine

HRID 1708930Notes

Reaction equation

HRID 1708930 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]1)[CH3:2].N.[H][H]>[Ni].CO>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][NH2:24])[CH2:20][CH2:21]1)[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 19911521HCID 19911521, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 199115154-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamineYield 52.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 41.8 parts of 4-[[3-(2-ethoxyethyl)-3H-imidazo-[4,5-b]pyridin-2-yl]methyl]-1-piperazineacetonitrile and 1100 parts of methanol, saturated with ammonia was hydrogenated at normal pressure and at room temperature with 20 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 converted into the (E)-2-butenedioate salt in 2-propanol. The salt was filtered off and crystallized from a mixture of acetonitrile and 2-propanol. The product was filtered off and dried, yielding 37.4 parts (52.1%) of 4-[[3-(2-ethoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]methyl]-1-piperazineethanamine; mp. 159.8° C. (compound 128).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe salt was filtered off
  4. customcrystallized from a mixture of acetonitrile and 2-propanol
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-4721cb15e2cf4374a24b317f0240b489
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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