Tetrahydrofuran → HCID 11652934, compound

HRID 1985036Notes

Reaction equation

HRID 1985036 reaction equation
ClC(O[O:5][CH2:6][CH:7]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]2[O:18][CH2:19][O:20][C:11]=2[CH:10]=1)[CH3:8])=O.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C1C[O:30][CH2:29]C1>>[CH2:19]1[O:18][C:12]2[CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]([CH:7]([CH3:8])[CH2:6][O:5][C:29]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:30])=[CH:10][C:11]=2[O:20]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8082PiperidineHCID 22280835HCID 22280835, compound

Product 1

HCID 11652934HCID 11652934, compoundYield 79%

Procedure

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.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in water
  4. washwashed with ether four times
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by silica gel chromatography (eluant: AcOEt/Hex, 1/4, v/v)

Sources & evidence

ORD record
ord-e9b6b757acf0460c89220b954f4043ec
Source dataset
uspto-grants-2009_06
Patent number
US07544829B2

Reaction notes

Loading…