3-[(4-methoxyphenyl)methyl]-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-3H-imidazo[4,5-b]-pyridine → 3-[(4-methoxyphenyl)methyl]-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridine

HRID 1904826Notes

Reaction equation

HRID 1904826 reaction equation
CC1C=CC(CNC2C(N)=CC=CC=2)=CC=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:29]3[N:28]=[C:27]2[CH2:35][CH:36]2[CH2:41][CH2:40][N:39](CC3C=CC=CC=3)[CH2:38][CH2:37]2)=[CH:21][CH:20]=1.[H][H]>[Pd].CO>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:26]2[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:29]3[N:28]=[C:27]2[CH2:35][CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 140133693-[(4-methoxyphenyl)methyl]-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-3H-imidazo[4,5-b]-pyridineHCID 14518103HCID 14518103, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 145180093-[(4-methoxyphenyl)methyl]-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 41 parts of 3-[(4-methoxyphenyl)methyl]-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-3H-imidazo[4,5-b]-pyridine and 480 parts of methanol was hydrogenated at normal pressure and at 50° C. with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 30 parts (89%) of 3-[(4-methoxyphenyl)methyl]-2-(4-piperidinylmethyl)-3H-imidazo[4,5-b]pyridine (37). In a similar manner there were also prepared:

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-0eb631fae0274aab8797c6595a6ede7e
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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