Ethanol → (-)-trans-1(2-Cyanoethyl)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-piperidine hydrochloride

HRID 467064

Reaktionsgleichung

Reaktionsgleichung von HRID 467064
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)=[CH:5][CH:4]=1.C(O)C.Br[CH2:30][CH2:31][C:32]#[N:33].C(=O)([O-])[O-].[K+].[K+]>C(OCC)C.CC(C)=O>[ClH:1].[C:32]([CH2:31][CH2:30][N:12]1[CH2:13][CH2:14][C@@H:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[C@H:10]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[CH2:11]1)#[N:33]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 170203-BromopropionitrileHCID 62878Paroxetine Hydrochloride

Produkt 1

HCID 67638429(-)-trans-1(2-Cyanoethyl)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-piperidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1 g of (-)-trans-4-(4-fluorophenyl)-3-(3,4-methylene dioxyphenoxymethyl)-piperidine hydrochloride in 50 ml 99 9% ethanol was mixed with 3-bromopropionitrile (7 ml) and 2 g potassium carbonate. The mixture was refluxed for 70 h. After cooling 25 ml acetone and 25 ml diethylether were added, the precipitate filtered off, and the filtrate evaporated in vacuo. The residue was extracted with 1N NaOH/ether, the ether layer dried (MgSO4) and evaporated to dryness. The residue was dissolved in acetone and excess conc. HCl was added. Subsequent evaporation gave a hard glass, which was purified on a silica gel column using 99.5% ethanol as eluent. The title compound was isolated, and its structure confirmed by the IR and NMR data. M.p. 156° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 70 h
  2. additionwere added
  3. filtrationthe precipitate filtered off
  4. customthe filtrate evaporated in vacuo
  5. extractionThe residue was extracted with 1N NaOH/ether
  6. dry with materialthe ether layer dried (MgSO4)
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in acetone
  9. additionexcess conc. HCl was added
  10. customSubsequent evaporation
  11. customgave a hard glass, which
  12. customwas purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-eb66a0f4ae404633a525c7dfed23e0e5
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158961

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