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

HRID 1713Notes

Reaction equation

HRID 1713 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:19]3[N:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:22][CH:21]=4)[C:17](=O)[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([O:36][CH3:37])[CH:15]=4)[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:38]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:19]3[N:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)=[CH:22][CH:21]=4)[CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[C:14]([O:36][CH3:37])[CH:15]=4)[C:10]=3[CH2:9][CH2:8][C:7]=2[CH:38]=1

Participants

4

Reactant 2

HCID 111240662,8-Dimethoxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-11,12-dihydro-6H-benzo[c]phenanthrid-6-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 110710862,8-Dimethoxy-5-[4-[2-(1-piperidinyl)ethoxy]phenyl]-11,12-dihydro-6H-benzo[c]phenanthridineYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customto return to room temperature
  2. temperaturebriefly warmed
  3. temperatureto reflux
  4. temperaturecooled
  5. customquenched with ethyl acetate (50 mL)
  6. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  7. dry with materialthe combined organic layers were dried (sodium sulfate)
  8. concentrationconcentrated
  9. customand purified via radial chromatography (silica gel, 1:1 hexane

Sources & evidence

ORD record
ord-9870787f9e3f4d56b73d33d54187af4f
Source dataset
uspto-grants-1998_03
Patent number
US05726186

Reaction notes

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