Bromobenzene → HCID 57686303, Verbindung

HRID 238261Notizen

Reaktionsgleichung

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[OH-].[Na+].[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:26]2[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=2)([CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Edukt 4

HCID 7961Bromobenzene

HCID 14798Sodium Hydroxide

HCID 6451240Aluminum(III) Chloride

HCID 108459131-Benzyl-4-methylpiperidin-4-ol

Produkt 1

HCID 57686303HCID 57686303, Verbindung

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 1-benzyl-4-methyl-piperidin-4-ol (0.4 g, 1.95 mmol) in bromobenzene (1.2 mL) was added aluminium trichloride (0.39 g, 2.9 mmol). The mixture was then heated to 100° C. for 14 hours and left standing at room temperature for 48 hours. Aqueous sodium hydroxide (1 N, 30 mL) was added and the products extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-25% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a brown oil (0.5 g). LCMS m/z 344.5 [M+H]+. R.T.=3.13 min (Analytical Method 4).

Aufarbeitung

waitleft
extractionthe products extracted into ethyl acetate
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent removed by evaporation under vacuum
customThe residue was purified by flash chromatography on silica eluting with 0-25% ethyl acetate/hexane
additionThe fractions containing the desired product
concentrationwere concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-a8ab2757a0024c21a9e4b7f76e8d0262
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642621B2

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