Hydrochloric Acid → 9-[(4-fluorophenyl)methyl]-1,9-dihydro-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-6H-purin-6-one

HRID 256677Notes

Reaction equation

HRID 256677 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:21]1)[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1.Cl.[OH-:34].[NH4+]>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:6]2[C:5]([CH2:19][CH:20]3[CH2:21][CH2:22][N:23]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24][CH2:25]3)=[N:4][C:3]3[C:2](=[O:34])[NH:10][CH:9]=[N:8][C:7]2=3)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 197852696-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-9H-purine

Product 1

HCID 1355888469-[(4-fluorophenyl)methyl]-1,9-dihydro-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-6H-purin-6-oneYield 52%

Procedure

A mixture of 3 parts of 6-chloro-9-[(4-fluorophenyl)methyl]-8-[[1-(phenylmethyl)-4-piperidinyl]-methyl]-9H-purine and 50 parts of a hydrochloric acid solution 1N was stirred and refluxed for 1.5 hours. After cooling, the mixture was made alkaline with ammonium hydroxide. The product was extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was crystallized from a mixture of acetonitrile and ethanol. The product was filtered off and dried, yielding 1.5 parts (52%) of 9-[(4-fluorophenyl)methyl]-1,9-dihydro-8-[[1-(phenylmethyl)-4-piperidinyl]methyl]-6H-purin-6-one; mp. 197.0° C. (compound 185).

Workup

  1. temperaturerefluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionThe product was extracted with trichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of acetonitrile and ethanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-0409098b259645268be7d124e32116bf
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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