2,4-Dimethylpyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-2,4-dimethyl-pyridinium bromide

HRID 84351

반응식

HRID 84351 반응식
[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][C:20]=1[CH3:26]>>[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][C:20]=2[CH3:26])=[CH:8][CH:9]=1

참가 물질

3

반응물 2

HCID 79362,4-DimethylpyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

생성물 1

HCID 247816821-[5-(1,1'-Biphenyl-4-yl)-pentyl]-2,4-dimethyl-pyridinium bromide수율 77%

반응 조건

온도
65 °C

실험 절차

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (331 mg, 1.09 mmol) and 2,4-lutidine (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 342 mg of the title compound. Yield: 77%. 1H NMR (300 MHz, CDCl3) δ 1.51 (m, 2H), 1.71 (m, 2H), 1.92 (m, 2H), 2.55 (s, 3H), 2.65 (t, J=7.8 Hz, 2H), 2.84 (s, 3H), 4.73 (t, J=7.8 Hz, 2H), 7.20-7.75 (m, 11H), 9.31 (d, J=6.3 Hz, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 20.1, 22.0, 25.8, 30.5, 30.8, 35.2, 57.4, 126.7, 126.9, 127.0, 128.2, 128.6, 128.8, 130.4, 138.5, 140.7, 140.9, 145.4, 152.8, 158.4 ppm.

후처리

  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

출처 및 근거

ORD 기록
ord-c95c51363e9a4dec813069f6fb6a614c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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