反応 #2446086

反応方程式

Ethyl iodide

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

K2CO3

ethyl iodide

→

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

溶媒

DCE

反応条件

後処理

1. 1
   温度the reaction mixture heated at 60° C. for another 24 hours
2. 2
   ろ過The reaction mixture was filtered
3. 3
   洗浄washed 5% methanol-DCM
4. 4
   濃縮The filtrate was concentrated
5. 5
   その他the crude material was purified by Combiflash® chromatography
6. 6
   洗浄eluting with 6-7% methanol/DCM

実験手順

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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