反应详情

温度

115 °C

A mixture of 1.3 g (4.1 mmol) 4-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester, 0.604 g (4.5 mmol) 4-cyclopropylaniline and 8.24 mL (8.24 mmol) dimethylaluminum chloride (1N in hexane) in 100 mL toluene was stirred at 115° C. for 15 h. After cooling to room temperature the mixture was poured into ice, the mixture was acidified with HCl aq. to pH=2 and extracted with ethyl acetate. The aqueous layer was basified with NaOH pellets to pH=8 and extracted with DCM. The combined organic layers were dried with MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica (amine) with a gradient formed from ethyl acetate and methanol to yield after evaporation of the product containing fractions 0.468 g (42%) of the title compound as light yellow solid. MS m/e: 270.0 [M+H]+.

1. temperatureAfter cooling to room temperature the mixture
2. additionwas poured into ice
3. extractionextracted with ethyl acetate
4. extractionextracted with DCM
5. dry with materialThe combined organic layers were dried with MgSO4
6. customevaporated to dryness
7. customThe residue was purified by column chromatography on silica (amine) with a gradient
8. customformed from ethyl acetate and methanol
9. customto yield
10. customafter evaporation of the product
11. additioncontaining fractions 0.468 g (42%) of the title compound as light yellow solid