Ethane, 1-fluoro-2-iodo- → 1-(2-Fluoroethyl)-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

HRID 1014268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014268
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].I[CH2:25][CH2:26][F:27]>O1CCCC1>[F:27][CH2:26][CH2:25][N:21]1[CH2:20][CH2:19][N:18]([CH:15]2[CH2:14][CH2:13][N:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:17][CH2:16]2)[CH2:23][CH2:22]1

Komponenten

4

Edukt 2

HCID 69804Ethane, 1-fluoro-2-iodo-2×HCID 598602641-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine2×

Produkt 1

HCID 598602761-(2-Fluoroethyl)-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazineAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (intermediate 8120, 18.03 g, 56.10 mmol and 2.23 g, 6.96 mmol from separate batches) in tetrahydrofuran was added 1-Iodo-2-fluoroethane (7.38 mL, 90.79 mmol). The reaction was stirred at 85° C. overnight. The solution was transferred to a sealed tube. Upon addition of 1-Iodo-2-fluoroethane (7.38 mL, 90.79 mmol), the reaction was stirred at 85° C. for an additional 5 hours. The solvent was removed in vacuo and the residue was taken up in water and extracted with dichloromethane (×3), dried with magnesium sulfate, filtered and concentrated. Purification by flash chromatography provided 1-(2-fluoroethyl)-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (15.94 g, 43.50 mmol, 69%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (qd, J=11.9, 3.7 Hz, 2 H) 1.79 (d, J=10.8 Hz, 2 H) 2.32-2.42 (m, J=7.0, 3.7 Hz, 9 H) 2.52 (dt, JHF=28.6 Hz, J=4.9 Hz 2 H) 2.86-2.95 (m, 2H) 3.85 (s, 3 H) 3.99 (d, J=13.4 Hz, 2 H) 4.46 (dt, JHF=47.8 Hz J=4.9 Hz 2 H), 6.45 (d, J=2.4 Hz, 1 H) 6.54 (dd, J=9.5, 2.6 Hz, 1 H) 7.82 (d, J=9.3 Hz, 1 H).

Aufarbeitung

  1. customThe solution was transferred to a sealed tube
  2. stirringthe reaction was stirred at 85° C. for an additional 5 hours
  3. customThe solvent was removed in vacuo
  4. extractionextracted with dichloromethane (×3)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d2205906f66f4b21b4561559eff4183f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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