[Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanone → alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

HRID 1736444

Reaktionsgleichung

Reaktionsgleichung von HRID 1736444
[S:1]1[C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2.[C:26]1([Li])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.C1CCCCC1.C(OCC)C>[C:16]1([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:6]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:5]3[S:1][C:2]4[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=4[CH:4]=3)[OH:7])[CH2:9][CH2:10]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

5

Edukt 2

HCID 18930331[Benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4-piperidinyl]methanoneHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 18930373alpha-[1-(2-Phenylethyl)-4-piperidinyl]-alpha-phenyl-2-benzo[b]thiophenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21895417Cyclohexane diethyletherLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Dissolve [benzo[b]thiophene-2-yl][1-(2-phenylethyl)-4piperidinyl]methanone (3.5 g, 10.01 mmol) in anhydrous tetrahydrofuran (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, phenyllithium (6 mL of a 2.0M solution in cyclohexane/ethyl ether, 12.0 mmol) and stir at -78° C. for 5 hours. Remove the ice bath and allow to warm to room temperature. Pour into saturated ammonium chloride (100 mL) and stir for 20 minutes. Separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, wash with water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl acetate/hexane) and recrystallize (isopropanol) to give the title compound as a white solid; mp 144°-146° C.

Aufarbeitung

  1. customRemove the ice bath
  2. temperatureto warm to room temperature
  3. additionPour into saturated ammonium chloride (100 mL)
  4. stirringstir for 20 minutes
  5. customSeparate the organic phase
  6. extractionextract the aqueous phase with ethyl acetate
  7. washwash with water
  8. dry with materialdry (MgSO4)
  9. customevaporate the solvent in vacuo
  10. customPurify by chromatography (50% ethyl acetate/hexane)
  11. customrecrystallize (isopropanol)

Quellen und Nachweise

ORD-Eintrag
ord-11482b46ee304cf6b30f0ab6f4f54a76
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541200

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