4-(Naphthalen-2-yl)piperidine → (S)-alpha-(2'-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzylidene)-gamma-butyrolactone

HRID 460657

Reaktionsgleichung

Reaktionsgleichung von HRID 460657
[O:1]1[CH2:18][C@H:2]1[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10].[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C(O)C>[OH:1][C@@H:2]([CH2:18][N:32]1[CH2:33][CH2:34][CH:29]([C:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)[CH2:30][CH2:31]1)[CH2:3][O:4][C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[CH:7]=[C:8]1[CH2:13][CH2:12][O:11][C:9]1=[O:10]

Komponenten

4

Edukt 2

HCID 220292644-(Naphthalen-2-yl)piperidineHCID 86585643(S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

Produkt 1

HCID 69497913(S)-alpha-(2'-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzylidene)-gamma-butyrolactoneAusbeute 53,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

(S)-α-(2′-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone (50 g) and 4-(naphthalen-2-yl)piperidine (43 g) were dissolved in ethanol (500 ml) and the mixture was refluxed under heating for 2 hr. After cooling, the solvent was evaporated under reduced pressure and the obtained crystals were collected by filtration. The crystals were recrystallized once from acetonitrile and once from a mixed solvent of ethyl acetate and ethanol to give the title compound (50 g), melting point 138–140° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. filtrationthe obtained crystals were collected by filtration
  6. customThe crystals were recrystallized once from acetonitrile and once from a mixed solvent of ethyl acetate and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-857f9eddc4a9439095e53212e9b9fd2f
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196199B2

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