Reaction #2446086

Reaction equation

Ethyl iodide

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

K2CO3

ethyl iodide

→

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

Solvents

DCE

Conditions

Workup

1. 1
   Temperaturethe reaction mixture heated at 60° C. for another 24 hours
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Washwashed 5% methanol-DCM
4. 4
   ConcentrationThe filtrate was concentrated
5. 5
   Otherthe crude material was purified by Combiflash® chromatography
6. 6
   Washeluting with 6-7% methanol/DCM

Procedure

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)

Source