Dimethylformamide → HCID 71226132, compound

HRID 2370027Notes

Reaction equation

HRID 2370027 reaction equation
[CH3:1][C:2]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[CH3:1][C:2]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][N:4]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 18419721Ethyl 3-methylpiperidine-3-carboxylate

Product 1

HCID 71226132HCID 71226132, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a round bottom flask was added ethyl 3-methylpiperidine-3-carboxylate (2.040 g, 11.91 mmol), 1-fluoro-4-nitrobenzene (1.765 g, 12.51 mmol), DMF (20 ml) and K2CO3 (2.140 g, 15.49 mmol). The reaction was stirred at 65° C. for 6 hrs. After this time, the reaction was diluted with EtOAc. The resulting solution was washed with water (2×) and saturated aqueous NaCl. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-30% EtOAc/Hex to give the product, ethyl 3-methyl-1-(4-nitrophenyl)piperidine-3-carboxylate (2.922 g, 9.90 mmol, 83% yield) as a yellow oily residue. Anal. Calcd. for C15H20N2O4 m/z 292.3, found: 293.2 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.10 (d, J=9.34 Hz, 2H), 6.87 (d, J=9.34 Hz, 2H), 4.18 (d, J=13.19 Hz, 1H), 4.11 (q, J=7.15 Hz, 2H), 3.80-3.58 (m, 1H), 3.00 (s, 1H), 2.90 (d, J=13.19 Hz, 1H), 2.40-2.23 (m, 1H), 1.75 (dd, J=8.52, 4.12 Hz, 2H), 1.42 (s, 1H), 1.26-1.14 (m, 6H).

Workup

  1. washThe resulting solution was washed with water (2×) and saturated aqueous NaCl
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified
  7. washeluting with a gradient of 0-30% EtOAc/Hex

Sources & evidence

ORD record
ord-3b938561a1fe457daf10a556bebf8385
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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