Tetrahydrofuran → HCID 11652934, compound

Participants

Reaction Steps

To 2-(3,4-methylenedioxy-6-nitrophenyl)propoxyl chloroformate (650 mg, 2.3 mmol) in dry THF (30 mL) was dropwisely added piperidine (800 μL, 8.1 mmol) in dry THF (20 mL). The reaction mixture was refluxed for 3 h and then stirred at r.t. overnight. The solvent was evaporated and the residue was dissolved in water and washed with ether four times. The organic extracts were combined and dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (eluant: AcOEt/Hex, 1/4, v/v). The collected fraction provided 2-(3,4-methylenedioxy-6-nitrophenyl)propoxycarbonyl piperidine (0.61 g, yield 79%). 1H-NMR (600 MHz, CDCl3): δ 7.21 (s, 1H, Ar—H), 6.79 (s, 1H, Ar—H), 6.01 (s, 2H, CH2), 4.12 (m, 2H, CH2), 3.71 (m, 1H, CH), 3.23 (s, 4H, CH2), 1.47 (m, 2H, CH2), 1.38 (s, 4H, CH2), 1.22 (d, 3H, J=6.6 Hz, CH3). 13C-NMR (150 MHz, CDCl3): δ 154.86 (OCOR), 151.50 (C ipso to NO2), 146.13 (C para to NO2), 143.89 (C para to CH(CH3)CH2OCOR), 134.59 (C ipso to CH(CH3)CH2OCOR), 106.75 (C ortho to CH(CH3)CH2OCOR), 105.02 (C ortho to NO2), 102.75 (OCH2O), 68.96 (CH2OCOR), 44.63 (Cα to ring N), 33.45 (CH), 25.47 (Cβ to ring N), 24.21 (Cγ to ring N), 17.78 (CH3). TLC: 33% ethyl acetate in hexanes, Rf=0.5.

Provenance & Evidence