Isoquinoline → 2-[5-(1,1'-Biphenyl-4-yl)-pentyl]-isoquinolinium bromide

HRID 84355

反応式

HRID 84355 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.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][N: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+:20]2[CH:21]=[CH:22][C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)=[CH:8][CH:9]=1

参加物

3

反応物 2

HCID 8405IsoquinolineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

生成物 1

HCID 685924742-[5-(1,1'-Biphenyl-4-yl)-pentyl]-isoquinolinium bromide収率 61%

反応条件

温度
65 °C

実験手順

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (322 mg, 1.06 mmol) and isoquinoline (1 mL) was heated at 60-70° C. for 12 hrs. The resulted 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 278 mg of the title compound. Yield: 61%. 1H NMR (300 MHz, CDCl3) δ 1.47 (m, 2H), 1.70 (m, 2H), 2.17 (m, 2H), 2.61 (t, J=7.5 Hz, 2H), 5.07 (t, J=7.5 Hz, 2H), 7.14-7.55 (m, 9H), 7.86 (m, 1H), 8.05 (m, 2H), 8.33 (d, J=6.9 Hz, 1H), 8.70 (d, J=8.1 Hz, 1H), 8.79 (dd, J=6.9, 0.6 Hz, 1H), 10.93 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 25.7, 30.7, 31.7, 35.2, 61.5, 126.3, 126.8, 126.9, 127.0, 127.7, 128.7, 128.8, 131.15, 131.22, 134.4, 136.9, 137.2, 138.5, 140.8, 141.0, 150.1 ppm.

後処理

  1. washThe resulted 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

出典と根拠

ORDレコード
ord-132aa4deb94144488e23001d10fe22b5
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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