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

HRID 84349

反応式

HRID 84349 の反応式
[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][CH:22]=[C:21]([CH3:25])[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][CH:22]=[C:21]([CH3:25])[CH:20]=2)=[CH:8][CH:9]=1

参加物

3

反応物 2

HCID 79703-MethylpyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

生成物 1

HCID 247816781-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3-methyl-pyridinium bromide収率 90%

反応条件

温度
65 °C

実験手順

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (358 mg, 1.18 mmol) and 3-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 421 mg of the title compound. Yield: 90%. 1H NMR (300 MHz, CDCl3) δ 1.45 (m, 2H), 1.70 (m, 2H), 2.08 (m, 2H), 2.59 (s, 3H), 2.63 (t, J=7.5 Hz, 2H), 4.92 (t, J=7.5 Hz, 2H), 7.18-7.58 (m, 9H), 7.94 (t, J=7.2 Hz, 1H), 8.17 (d, J=8.1 Hz, 1H), 9.26 (d, J=6.3 Hz, 1H), 9.46 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 18.8, 25.7, 30.7, 31.9, 35.2, 61.5, 126.8, 126.9, 127.0, 127.7, 128.3, 128.7, 128.8, 138.5, 139.5, 140.7, 141.1, 142.1, 144.5, 145.5 ppm.

後処理

  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

出典と根拠

ORDレコード
ord-a7b4c74cdede4cfc8769a641e5eee143
出典データセット
uspto-grants-2014_09
特許番号
US08846937B2

関連ノート

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