3,5-Dimethylpyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3,5-dimethyl-pyridinium bromide

HRID 84353

Reaktionsgleichung

Reaktionsgleichung von HRID 84353
[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]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[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]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=2)=[CH:8][CH:9]=1

Komponenten

3

Edukt 2

HCID 115653,5-DimethylpyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

Produkt 1

HCID 247816861-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3,5-dimethyl-pyridinium bromideAusbeute 85 %

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (352 mg, 1.16 mmol) and 3,5-lutidine (1 mL) was heated at 60-70° C. for 12 hrs. The resulting 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 406 mg of the title compound. Yield: 85%. 1H NMR (300 MHz, CDCl3) δ 1.45 (m, 2H), 1.70 (m, 2H), 2.08 (m, 2H), 2.53 (s, 6H), 2.63 (t, J=7.8 Hz, 2H), 4.84 (t, J=7.5 Hz, 2H), 7.18-7.58 (m, 9H), 7.93 (s, 1H), 9.21 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 18.6, 25.8, 30.8, 31.9, 35.2, 61.3, 126.8, 126.9, 127.0, 128.7, 128.8, 138.4, 138.7, 140.7, 141.1, 141.7, 146.0 ppm.

Aufarbeitung

  1. washThe resulting 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-e58db41c818244c2ae2603257cd342bb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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