Реакция #2132575

Уравнение реакции

2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

2,6-dimethyl-morpholine

N,N-dimethylglycine hydrochloride

potassium carbonate

→

2-[3-(2,6-dimethyl-morpholin-4-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

Выход 80.4%

Растворители

dimethyl sulfoxide

Условия реакции

Обработка

1. 1
   ТемператураThen the reaction mixture cooled to room temperature
2. 2
   ЭкстракцияThe reaction mixture was extracted with ethyl acetate (2×200 mL)
3. 3
   Промывкаwashed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL)
4. 4
   Сушкаdried over anhydrous sodium sulfate
5. 5
   Концентрированиеconcentrated in vacuo

Методика

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (4.0 g, 10.3 mmol), 2,6-dimethyl-morpholine (6.4 mL, 51.6 mmol), copper(I) iodide (785 mg, 4.1 mmol), N,N-dimethylglycine hydrochloride (1.2 g, 8.2 mmol) and potassium carbonate (4.3 g, 30.9 mmol) in dimethyl sulfoxide (20 mL) was stirred at 120° C. for 16 hours. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×200 mL), washed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[3-(2,6-dimethyl-morpholin-4-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.5 g, 80%) as a white solid which was used for next step without further purification: LC/MS m/e calcd for C26H34N2O3 (M+H)+: 423.57, observed: 423.0.

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