Reaktion #2446086

Reaktionsgleichung

Ethyl iodide

benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester

K2CO3

ethyl iodide

→

1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture heated at 60° C. for another 24 hours
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Waschenwashed 5% methanol-DCM
4. 4
   EinengenThe filtrate was concentrated
5. 5
   Sonstigethe crude material was purified by Combiflash® chromatography
6. 6
   Wascheneluting with 6-7% methanol/DCM

Vorschrift

To a stirred solution of benzoic acid 2-cyclohexylamino-1-methyl-ethyl ester (1.0 g, 3.8 mmol) in DCE (20 mL) were added successively K2CO3 (2.11 g, 15.2 mmol) and ethyl iodide (1.8 mL, 22 mmol). The resulting mixture was heated at 50° C. for 16 hours in a sealed tube. Ethyl iodide (1.8 mL) was again added and the reaction mixture heated at 60° C. for another 24 hours. The reaction mixture was filtered and washed 5% methanol-DCM. The filtrate was concentrated and the crude material was purified by Combiflash® chromatography eluting with 6-7% methanol/DCM to provide 1-(cyclohexyl(ethyl)amino)propan-2-yl benzoate. Yield: 1.04 g (94.70%). 1H NMR (DMSO-d6) δ 7.95 (d, J=7 Hz, 2 H), 7.64 (t, J=7 Hz, 1 H), 7.52 (t, J=8 Hz, 2 H), 5.08-5.04 (m, 1 H), 2.68-2.62 (m, 1 H), 2.55-2.40 (m, 4 H), 1.70-1.53 (m, 5 H), 1.26 (d, J=6 Hz, 3 H), 1.19-1.07 (m, 5 H), 0.93 (t, J=7 Hz, 3 H). LCMS: m/z=290.4 [M+H], RT=3.93 min, (Column: Y, Program: P1)

Quelle