Hydrochloric Acid → 6-[(2,2-Diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamide

HRID 1168287Notes

Reaction equation

HRID 1168287 reaction equation
[C:1]1([CH:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3C2CCCCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)C>[C:36]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 102809386-[(2,2-Diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carboxamide

Product 1

HCID 1785234056-[(2,2-Diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamideYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-[(2,2-diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9-tetrahydro-2H-pyran-2-yl-9H-purine-2-carboxamide (Preparation 10) (420 mg, 0.76 mmol) in ethanol (20 ml) was treated with 2 M aqueous hydrochloric acid (0.9 ml). The mixture was heated under reflux for 30 minutes after which time a white precipitate had formed. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and 10% weight by volume aqueous ammonia. The organic phase was separated, dried (anhydrous magnesium sulphate), filtered and evaporated under reduced pressure to afford the title compound as a white solid (319 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes after which time a white precipitate
  3. customhad formed
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was partitioned between dichloromethane and 10% weight by volume aqueous ammonia
  6. customThe organic phase was separated
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0e709d01e1cb46cb9a9da37fb3e84b8f
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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