9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]oxy]-9H-purine → 9-[(4-fluorophenyl)methyl]-8-(4-piperidinyloxy)-9H-purine

HRID 256659Notes

Reaction equation

HRID 256659 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([O:18][CH:19]3[CH2:24][CH2:23][N:22](CC4C=CC=CC=4)[CH2:21][CH2:20]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=[CH:4][CH:3]=1.[H][H]>[Pd].[Ni].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([O:18][CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 197852369-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]oxy]-9H-purineHCID 178418361HCID 178418361, compound

Product 1

HCID 197852399-[(4-fluorophenyl)methyl]-8-(4-piperidinyloxy)-9H-purineYield 82.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 16.25 parts of 9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]oxy]-9H-purine and 200 parts of methanol was hydrogenated at normal pressure and at 50° C. with 3 parts of palladium-on-charcoal catalyst 10% and 6 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 taken up in trichloromethane and water was added. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was stirred in 1,1'-oxybisethane. The precipitated product was filtered off and dried, yielding 10.5 parts (82.2%) of 9-[(4-fluorophenyl)methyl]-8-(4-piperidinyloxy)-9H-purine; mp. 79.3° C. (compound 56).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionwater was added
  4. extractionThe product was extracted with trichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe precipitated product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-73ca9048d64547b1a7a33f0e22f33de5
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

Loading…