Methane → α-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-α-phenyl-2-benzothiazolemethanol

HRID 1450433

Reaktionsgleichung

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)=[O:11].[C:28]1([Li])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C>O1CCCC1.C1CCCCC1.C(OCC)C.C(Cl)Cl>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:15]2[CH2:16][CH2:17][CH:12]([C:10]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[OH:11])[CH2:13][CH2:14]2)=[CH:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Dissolve [2-benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4piperidinyl]methanone (2.0 g, 5.26 mmol) in anhydrous tetrahydrofuran (50 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, phenyllithium (3.16 mL of a 2.0M solution in cyclohexane/ethyl ether, 6.31 mmol). Stir at -78° C. for 30 minutes, quench with saturated ammonium chloride (100 mL), separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (75% ethyl acetate/hexane) to give a yellow oil. Dissolve the oil in methylene chloride and treat with activated charcoal.

Aufarbeitung

customquench with saturated ammonium chloride (100 mL)
customseparate the organic phase
extractionextract the aqueous phase with ethyl acetate
dry with materialdry (MgSO4)
customevaporate the solvent in vacuo
customPurify by chromatography (75% ethyl acetate/hexane)
customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag: ord-02ba4ab3b5fc4113948ac9c575a83229
Quelldatensatz: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05602147

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