Piperidine → HCID 18173112, compound

HRID 395882Notes

Reaction equation

HRID 395882 reaction equation
O[CH:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([C:10]1[NH:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=3[N:11]=1)[CH2:6]2.CC1(C)[O:35][C:33](=[O:34])[CH2:32][C:30](=[O:31])[O:29]1.N1CCCCC1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[O:23]=[C:14]1[N:13]([CH2:24][CH2:25][CH3:26])[C:12]2[N:11]=[C:10]([CH:5]3[CH2:4][CH:3]4[CH:2]([CH:32]([C:33]([OH:35])=[O:34])[C:30]([OH:31])=[O:29])[CH:7]([CH2:8][CH2:9]4)[CH2:6]3)[NH:18][C:17]=2[C:16](=[O:19])[N:15]1[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 10155447HCID 10155447, compound

Product 1

HCID 18173112HCID 18173112, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-(8-Hydroxy-bicyclo[3.2.1]oct-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (30 mg) taken in CHCl3 (5 ml). To this solution Meldrum's acid (58 mg), piperidine (10 mg) were added and heated to reflux overnight. The next day, after cooling to room temperature, diluted with ethyl acetate, washed with 1N HCl, sat NaHCO3, brine, and dried. The solvent was removed under reduced pressure, the crude residue was taken up in MeOH, cooled to 0° C., NaBH4 (30 mg) was added, the mixture was stirred for 15 min. The reaction was diluted with 1N HCl, extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated. The residue was taken up in THF (5 ml) and 4N HCl (5 ml) was added and stirred for 1 day. The reaction mixture was extracted with ethyl acetate, washed with brine, and concentrated. The crude product was purified by HPLC. Yield (6 mg). Mass (ES+ 447).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. washwashed with 1N HCl
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. temperaturecooled to 0° C.
  7. additionNaBH4 (30 mg) was added
  8. additionThe reaction was diluted with 1N HCl
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated
  13. addition4N HCl (5 ml) was added
  14. stirringstirred for 1 day
  15. extractionThe reaction mixture was extracted with ethyl acetate
  16. washwashed with brine
  17. concentrationconcentrated
  18. customThe crude product was purified by HPLC
  19. customYield (6 mg)

Sources & evidence

ORD record
ord-0d25866a3e7344ea9137579dbc7769dd
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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