Reaktion #171537

Reaktionsgleichung

4-(5-bromopentyl)-1,1′-biphenyl

isoquinoline

→

title compound

Ausbeute 61.0%

2-[5-(1,1′-biphenyl-4-yl)-pentyl]-isoquinolinium bromide

Ausbeute 61.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe resulted mixture was washed with diethyl ether
2. 2
   workup.DISSOLUTIONdissolved in water (30 mL)
3. 3
   ExtraktionThe aqueous solution was extracted with ethyl acetate (30 mL×5)
4. 4
   SonstigeWater was removed by lyophilization

Vorschrift

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.

Quelle