反应详情

温度

50 °C

A mixture of 2-bromo-6-(piperidine-1-carbonyl)-cyclohexanone (20; prepared according to example 3(b)) (500 mg, 1.7 mmol) and (2-fluoro-ethyl)-phenyl-amine (24) (890 mg, 3.5 mmol) was stirred under N2 at 50° C. for 3 h and the reaction turned brown. The resulting mixture was dissolved in propan-2-ol (2 mL) and dry zinc chloride (682 mg, 5 mmol) was added. The mixture was heated to reflux under N2 for 16 h and then concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with 2 N HCl (20 mL), water (2×20 mL) and aqueous potassium carbonate solution (2×20 mL) then dried and concentrated in vacuo. The crude material was triturated with diethyl ether to afford 151 mg (27%) of [9-(2-fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazol-4-yl]-piperidin-1-yl-methanone (non-radioactive imaging agent 6) as a white solid. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 21.6, 21.8, 24.7, 26.5, 26.9, 27.4, 37.3, 43.1 (d, JCF=45 Hz), 47.0, 82.1 (d, JCF=173 Hz), 108.5, 108.9, 118.6, 119.4, 121.0, 126.8, 136.2, 172.7.

1. temperatureThe mixture was heated
2. temperatureto reflux under N2 for 16 h
3. concentrationconcentrated in vacuo
4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
5. washwashed with 2 N HCl (20 mL), water (2×20 mL) and aqueous potassium carbonate solution (2×20 mL)
6. customthen dried
7. concentrationconcentrated in vacuo
8. customThe crude material was triturated with diethyl ether