반응 #1809

반응 방정식

product

2,8-Dimethoxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-11,12-dihydro-6H-benzo[c]phenanthrid-6-one

lithium aluminum hydride

→

title compound

수율 72.4%

2,8-Dimethoxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-11,12-dihydro-6H-benzo[c]phenanthridine

수율 72.4%

용매

THF

반응 조건

후처리

1. 1
   기타to return to room temperature
2. 2
   온도briefly warmed
3. 3
   온도to reflux
4. 4
   온도cooled
5. 5
   기타quenched with ethyl acetate (50 mL)
6. 6
   추출The aqueous layer was extracted with ethyl acetate (2×50 mL)
7. 7
   건조the combined organic layers were dried (sodium sulfate)
8. 8
   농축concentrated
9. 9
   기타and purified via radial chromatography (silica gel, 1:1 hexane

실험 절차

A solution of the product of Example 12 (350 mg, 0.69 mmol) in THF (25 mL) was treated with lithium aluminum hydride (129 mg, 3.4 mmol) inducing a moderate exotherm. The mixture was allowed to return to room temperature and stirred for 2 h, then briefly warmed to reflux, cooled, and quenched with ethyl acetate (50 mL) followed by saturated ammonium chloride (50 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined organic layers were dried (sodium sulfate), concentrated; and purified via radial chromatography (silica gel, 1:1 hexane:ethyl acetate, 5% methanol, under an ammonia atmosphere) to provide 248 mg (64%) of the title compound as a yellow foam: 1H NMR (300 MHz, CDCl3) δ7.28 (d, J=8.5 Hz, 1H), 7.05 (d, J=8.5 Hz, 1H), 6.79 (m, 3H), 6.72 (d, J=2.6 Hz, 1H), 6.65 (d, 9.0 Hz, 2H), 6.58 (d, J=2.6 Hz, 1H), 6.52 (dd, J=8.6, 2.6 Hz, 1H), 4.65 (s, 2H), 3.94 (t, J=6.1 Hz, 2H), 3.74 (s, 3H), 3.74 (s, 3H), 2.96 (dd, J=8.3, 5.6, 2H), 2.81 (dd, J=8.3, 5.9 Hz, 2H), 2.66 (t, J=6.1 Hz, 2H), 2.43 (m, 4H), 1.5-1.6 (m, 4H), 1.3-1.5 (m, 2H); 13C NMR (75 MHz, CDCl3) δ158.5, 158.3, 153.3, 141.7, 138.4, 134.6, 132.3, 126.6, 126.2, 125.3, 122.9, 121.7, 120.5, 114.9, 113.4, 112.3, 111.2, 111.0, 65.8, 57.8, 55.6, 55.2, 55.1, 54.8, 29.0, 25.7, 24.0, 22.2; IR (CHCl3) 1610, 1506 cm-1 ; MS (FD) m/e 496 (M+); Anal. calc'd. for C32H36N2O3 : C, 77.37; H, 7.32; N, 5.64. Found: C, 77.25; H, 7.12; N, 5.75.

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