Quinoline → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-quinolinium bromide

HRID 84354

반응식

HRID 84354 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[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[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[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:9]=1

참가 물질

3

반응물 2

HCID 7047QuinolineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

생성물 1

HCID 247816881-[5-(1,1'-Biphenyl-4-yl)-pentyl]-quinolinium bromide수율 64%

반응 조건

온도
65 °C

실험 절차

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (328 mg, 1.08 mmol) and quinoline (1 mL) was heated at 60-70° C. for 12 hrs. The resulting mixture was washed with diethyl ether and then dissolved in water (30 mL). The aqueous solution was extracted with ethyl acetate (30 mL×5). Water was removed by lyophilization to afford 297 mg of the title compound. Yield: 64%. 1H NMR (300 MHz, CDCl3) δ 1.58 (m, 2H), 1.70 (m, 2H), 2.13 (m, 2H), 2.62 (t, J=7.5 Hz, 2H), 5.37 (t, J=7.8 Hz, 2H), 7.14-7.58 (m, 9H), 7.92 (d, J=7.5 Hz, 1H), 8.17 (m, 2H), 8.36 (m, 2H), 9.13 (d, J=8.4 Hz, 1H), 10.33 (d, J=5.4 Hz, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 26.1, 30.3, 30.9, 35.2, 58.1, 118.3, 122.5, 126.8, 126.9, 127.1, 128.7, 128.8, 129.9, 130.1, 131.1, 136.0, 137.5, 138.5, 140.7, 141.0, 147.3, 150.1 ppm.

후처리

  1. washThe resulting mixture was washed with diethyl ether
  2. dissolutiondissolved in water (30 mL)
  3. extractionThe aqueous solution was extracted with ethyl acetate (30 mL×5)
  4. customWater was removed by lyophilization

출처 및 근거

ORD 기록
ord-a541452adc49488e88f1c3531f9f2a58
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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