Reaktion #426592

Reaktionsgleichung

2-methylcyclohexanamine

2,3,5,6-tetrafluoro-p-toluic acid

HOBt

EDCI

→

title compound

Ausbeute 90.0%

2,3,5,6-tetrafluoro-4-methyl-N-(2-methylcyclohexyl)benzamide

Ausbeute 90.0%

Lösungsmittel

DMF

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto slowly warm to ambient temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   Waschenwashed with 1N HCl, water, aqueous NaHCO3, water and brine
4. 4
   Trocknendrying over MgSO4, filtration and removal of solvent in vacuo
5. 5
   Sonstigeafforded
6. 6
   Sonstigethe crude product as a pale yellow solid Recrystallization (EtOH/H2O)
7. 7
   Sonstigedrying in vacuo

Vorschrift

2,3,5,6-tetrafluoro-p-toluic acid (4.00 g, 19.22 mmol), HOBt (5.19 g, 38.44 mmol) and EDCI (4.42 g 23.06 mmol) were mixed in 200 ml of anhydrous DCM and 30 ml of anhydrous DMF. The mixture was cooled to 0° C. and allowed to stir under Ar for 15 minutes. To the mixture was added 2-methylcyclohexanamine (3.05 mL, 23.06 mmol) and the reaction mixture was allowed to slowly warm to ambient temperature and stirred overnight. The reaction mixture was diluted with DCM, washed with 1N HCl, water, aqueous NaHCO3, water and brine, drying over MgSO4, filtration and removal of solvent in vacuo, afforded the crude product as a pale yellow solid Recrystallization (EtOH/H2O) and drying in vacuo gave 5.23 g of the title compound as a white solid (mixture of 2 diasteromers, 90%). 1H NMR (CDCl3) δ 0.95, 1.01 (d, J=7.0, 6.6 Hz, 3H) 1.1-2.1 (m, 9H), 2.29 (m, 3H), 3.70, 4.29 (m, 1H), 5.65, 5.92 (m, 1H). MS (304.1, M+H). m. p. 202-204° C.

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