반응 #2446086

반응 방정식

Ethyl iodide

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

K2CO3

ethyl iodide

→

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

용매

DCE

반응 조건

후처리

1. 1
   온도the reaction mixture heated at 60° C. for another 24 hours
2. 2
   여과The reaction mixture was filtered
3. 3
   세척washed 5% methanol-DCM
4. 4
   농축The filtrate was concentrated
5. 5
   기타the crude material was purified by Combiflash® chromatography
6. 6
   세척eluting with 6-7% methanol/DCM

실험 절차

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)

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