Potassium Carbonate → (S)-N-(2,3-dihydrofuro[3,2-f]-1,4-benzodioxin-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine monofumarate monohydrate

HRID 275781

Reaktionsgleichung

Reaktionsgleichung von HRID 275781
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][NH2:22])[CH2:17][CH2:16]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>C(#N)C.C(O)C>[OH2:2].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[O:28]1[C:26]2[C:25]3[CH:24]=[CH:23][O:30][C:10]=3[CH:9]=[CH:14][C:1]=2[O:4][CH2:11][C@@H:12]1[CH2:13][NH:22][CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])[CH2:16][CH2:17]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 10608971(1-(2-Methoxyphenyl)piperidin-4-yl)methanamine

Produkt 1

HCID 22951199(S)-N-(2,3-dihydrofuro[3,2-f]-1,4-benzodioxin-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine monofumarate monohydrateAusbeute 187 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of the product from the previous reaction (2.80 g), potassium carbonate (10.0 g) and 1-[(2-methoxyphenyl)piperid-4-yl]methylamine (1.88 g) in dry acetonitrile (100 ml) was heated under reflux with stirring for 90 hours. The cooled mixture was filtered and the filtrate evaporated under reduced pressure to leave a pale-yellow oil. Purification by flash column chromatography on silica eluting with a 19:1 mixture of dichloromethane and methanol gave a pale-yellow oil which was then dissolved in ethanol (5 ml) and treated with a solution of fumaric acid (0.70 g) in ethanol (5 ml). The solvent was evaporated from the resulting solution under reduced pressure to give (S)-N-(2,3-dihydrofuro[3,2-f]-1,4-benzodioxin-2-ylmethyl)-1-[1-(2-methoxyphenyl)piperid-4-yl]methylamine monofumarate monohydrate (3.06 g) as a pale-yellow solid m.p. 95-6° C., [α]D =−38.5° (C=0.301, MeOH).

Aufarbeitung

  1. additionA mixture of the product
  2. temperaturewas heated
  3. temperatureunder reflux
  4. filtrationThe cooled mixture was filtered
  5. customthe filtrate evaporated under reduced pressure
  6. customto leave a pale-yellow oil
  7. customPurification by flash column chromatography on silica eluting
  8. additionwith a 19:1 mixture of dichloromethane and methanol
  9. customgave a pale-yellow oil which
  10. customThe solvent was evaporated from the resulting solution under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bb2a303317954c228bf43deb7b1dede9
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353002B2

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