Methyl indole-7-carboxylate → Methyl 1-((1-phenylpiperidin-4-yl)methyl)-1H-indole-7-carboxylate

HRID 1909885

Reaktionsgleichung

[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13]O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[C:24]([O:26][CH3:27])=[O:25])[CH:17]=[CH:16]1.C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[C:24]([O:26][CH3:27])=[O:25])[CH:17]=[CH:16]3)[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of (1-phenylpiperidin-4-yl)methanol (958 mg), methyl 1H-indole-7-carboxylate (590 mg), and toluene (20 mL) was added (tributylphosphoranylidene)acetonitrile (1.0 g) at room temperature. The mixture was stirred at 100° C. for 1 day. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 1-[(1-phenylpiperidin-4-yl)methyl]-1H-indole-7-carboxylate (163 mg).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-a42d8d0904a242ed9ef58cd3e12324b9
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08598355B2

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