Sodium Carbonate → 1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazine

HRID 419430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419430
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1.[F:25][CH:26](I)[CH3:27].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:20][CH2:21][N:22]([CH2:27][CH2:26][F:25])[CH2:23][CH2:24]2)[CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 23510620IodofluoroethaneHCID 594529121-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Produkt 1

HCID 594527481-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazineAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (0.050 g, 1.41 mmol), 1-fluoroethyliodide (0.229 mL, 2.82 mmol), Na2CO3 (0.179 g, 1.69 mmol) were taken up in acetonitrile (10 mL), heated to 70° C. and stirred overnight. Reaction mixture was cooled and then poured onto prepackaged silica gel cartridge and dried by vacuum suction of air through cartridge and then flash chromatographed to give the title compound of step E (0.370 g, 65%). MS (M+H, ES+) 401.

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas cooled
  3. additionpoured onto prepackaged silica gel cartridge
  4. customdried by vacuum suction of air through cartridge
  5. customflash chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-88da2d8f38ba4dcbac4493199108dbd6
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

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