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Piperidine → Piperiacetildenafil

HRID 21924
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 21924
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:31][CH2:32][CH3:33])=[C:15]([C:17]2[NH:18][C:19](=[O:30])[C:20]3[N:25]([CH3:26])[N:24]=[C:23]([CH2:27][CH2:28][CH3:29])[C:21]=3[N:22]=2)[CH:16]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:32]([O:31][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[CH2:8][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:16][C:15]=1[C:17]1[NH:18][C:19](=[O:30])[C:20]2[N:25]([CH3:26])[N:24]=[C:23]([CH2:27][CH2:28][CH3:29])[C:21]=2[N:22]=1)[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 1357385501,4-Dihydro-5-[5-bromoacetyl)-2-ethoxyphenyl]-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

Produkt 1

HCID 135564757PiperiacetildenafilAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Piperidine (0.22 ml, 0.0022 mol) was added to a stirred suspension of 5-(5-bromoacetyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Preparation 8, 0.95 g, 0.0022 mol) and anhydrous potassium carbonate (0.6 g, 0.0044 mol) in acetonitrile (50 ml) at room temperature. After 18 hours the mixture was evaporated under vacuum, the residue dissolved in water (50 ml) and the solution extracted with ethyl acetate (3×30 ml). The organic extracts were combined, washed with brine (3×20 ml), dried (Na2SO4) and evaporated under vacuum. The resulting yellow solid was chromatographed on silica gel (12g), using a methanol in dichloromethane elution gradient (0-2% methanol), to give an off-white solid. Crystallisation from ethyl acetate-hexane gave the title compound as an off-white powder (0.27 g, 28%), m.p. 149°-151° C. Found: C,66.13; H,6.90; N,15.95. C24H31N5O5 requires C,65,88; H,7.14; N,16.01%.

Aufarbeitung

  1. customAfter 18 hours the mixture was evaporated under vacuum
  2. dissolutionthe residue dissolved in water (50 ml)
  3. extractionthe solution extracted with ethyl acetate (3×30 ml)
  4. washwashed with brine (3×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum
  7. customThe resulting yellow solid was chromatographed on silica gel (12g)
  8. washa methanol in dichloromethane elution gradient (0-2% methanol)
  9. customto give an off-white solid
  10. customCrystallisation from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-63913ca8d35f4e0797208f116ed09fcf
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05426107

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