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ethyl 1-(2-chloropyrimidin-4-yl)piperidine-4-carboxylate[ No CAS ]
[ 1208087-83-5 ]
Yield
Reaction Conditions
Operation in experiment
8.87 g
With water; sodium hydroxide; In methanol; at 20.0℃; for 4.0h;
To a solution of the compound obtained in the previous step (10 g, 37.07 mmol) in MeOH (70 ml) was added a 1 N aqueous solution of NaOH (35 ml) and the reaction mixture was stirred at room temperature for 4h. The reaction mixture was concentrated under reduced pressure and acidified by the addition of a 2M aqueous solution of HCI. The aqueous mixture was extracted with CH2Cl2:MeOH (9:1 ). The combined organic layers were dried over Na2S04 andconcentrated under reduced pressure to give 1 -(2-chloropyrimidin-4-yl)piperidine-4-carboxylic acid (8.87 g) as a white solid.
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 17.0h;
To a suspension of the compound obtained in the previous step (8.87 g, 36.7 mmol) in dichloromethane (300 ml) were added Nu,Nu-diisopropylethyl amine (14.23 g, 1 10.1 mmol), 3,5- dimethoxyaniline (16.87 g, 1 10.1 mmol) and TBTU (17.68 g, 55.1 mmol). After stirring for 17h at room temperature the reaction mixture quenched by the addition of a saturated aqueous solution of sodiumbicarbonate and extracted with dicloromethane. The combined organic layers were dried over Na2S04 and evaporated under reduced pressure. The crude product was purified by normal phase chromatography, eluting with Heptane with 50% ethyl acetate to give 1 -(2-chloropyrimidin-4-yl)-N-(3,5-dimethoxyphenyl)piperidine-4-carboxamide (6.99 g) as a white solid
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