4-Methylpyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-4-methyl-pyridinium bromide

HRID 84350

Reaktionsgleichung

Reaktionsgleichung von HRID 84350
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[N:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>>[Br-:1].[C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N+:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:8][CH:9]=1

Komponenten

3

Edukt 2

HCID 79634-MethylpyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

Produkt 1

HCID 247816801-[5-(1,1'-Biphenyl-4-yl)-pentyl]-4-methyl-pyridinium bromideAusbeute 86 %

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (348 mg, 1.15 mmol) and 4-picoline (1 mL) was heated at 60-70° C. for 12 hrs. The resulted mixture was washed with diethyl ether and then dissolved in water (15 mL). The aqueous solution was extracted with diethyl ether (30 mL×3). Water was removed by lyophilization to afford 391 mg of the title compound. Yield: 86%. 1H NMR (300 MHz, CDCl3) δ 1.42 (m, 2H), 1.69 (m, 2H), 2.04 (m, 2H), 2.57 (s, 3H), 2.62 (t, J=7.2 Hz, 2H), 4.85 (t, J=7.2 Hz, 2H), 7.15-7.62 (m, 9H), 7.82 (d, J=6.0 Hz, 2H), 9.25 (d, J=6.0 Hz, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 22.3, 25.5, 30.7, 31.6, 35.2, 61.0, 126.8, 126.9, 127.1, 128.7, 128.8, 128.9, 138.5, 140.7, 141.1, 144.0, 158.7 ppm.

Aufarbeitung

  1. washThe resulted mixture was washed with diethyl ether
  2. dissolutiondissolved in water (15 mL)
  3. extractionThe aqueous solution was extracted with diethyl ether (30 mL×3)
  4. customWater was removed by lyophilization

Quellen und Nachweise

ORD-Eintrag
ord-080fd969e768478ab418058ed447ff5d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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