Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties
An effective dose and compound technology, applied in the direction of organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve problems such as increasing the variability of compound formulations
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Embodiment 1-d2
[0220] Example 1-d 2 -Benzo[1,3]dioxol-5-carbaldehyde (d 2 - piperonal)
[0221]
[0222] To Cs in DMF (60mL) 2 CO 3 (11.6 g, 35.6 mmol) was added 3,4-dihydroxybenzaldehyde (3.30 g, 23.9 mmol). The mixture was evacuated and flushed three times with nitrogen. Then add CD at room temperature 2 Cl 2 (2.29 mL, 26.3 mmol, 99.9% D). The reaction mixture was heated at 110°C for 2 hours, cooled to ambient temperature and partitioned between water and diethyl ether-pentane. The organic layer was washed with water more than 3 times and dried (MgSO 4 ), concentrated to give the desired product d as an off-white solid 2 -Piperonal.
[0223] Yield: 2.21 g (14.5 mmol, 61%, 94% D incorporation at the methylenedioxy group). 1 H-NMR (CDCl 3 ) δppm: 6.06 (s, 0.12H); 6.93 (m, 1H); 7.33 (m, 1H); 7.41 (m, 1H); 9.80 (s, 1H).
Embodiment 2-d2
[0224] Example 2-d 2 -Benzo[1,3]dioxol-5-ol (d 2 -sesamol)
[0225]
[0226] To d in MeOH (20 mL) 2 - Piperonal (2.21 g, 14.5 mmol, 94% D-introduction at the methylenedioxy group) suspension was added H 2 o 2 (2.1 mL, 30% in water). The mixture was dissolved in H in MeOH (4 mL) 2 SO 4 (0.2 mL, concentrated aqueous solution) was treated and stirred at room temperature for 14 hours. The reaction mixture was partitioned between water and ether-pentane. The organic layer was washed more than 5 times with water and dried (MgSO 4 ) and concentrate. The residue was further purified by column chromatography on silica gel (95 g) using 10% EtOAc in hexanes as eluent to give the desired product d as a white solid 2 - Sesamol.
[0227] Yield: 1.12 g (55%, 8.00 mmol, 94% D-incorporation at the methylenedioxy group). 1 H-NMR (CDCl 3) δppm: 5.89 (s, 0.12H); 6.23 (m, 1H); 6.42 (m, 1H); 6.63 (m, 1H).
Embodiment 3
[0228] Example 3-methanesulfonic acid trans-(4R, 3S)-4-(4-fluorophenyl)-1-methyl-piperidin-3-ylmethyl ester
[0229]
[0230] to the anhydrous CH 2 Cl 2 trans-(4R,3S)-[4-(4-fluoro-phenyl)-1-methyl-piperidin-3-yl]-methanol (1.00 g, 4.48 mmol, 3B Medical Systems ) solution by adding Et 3 N (1.5 mL). The mixture was cooled to 0° C. and treated with methanesulfonyl chloride (0.57 mL) and stirred in an ice bath for 0.5 hours, then at room temperature for an additional 1.5 hours. The reaction mixture was filtered through a cotton plug and additional anhydrous CH 2 Cl 2 (10 mL) to wash. The organic layer was washed with diethyl ether (100 mL) and additional CH in a separatory funnel 2 Cl 2 (20mL) diluted and washed 3 times with water (10mL each time), dried (MgSO 4 ), and concentrated to give the desired product trans-(4R,3S)-4-(4-fluorophenyl)-1-methyl-piperidin-3-ylmethyl methanesulfonate.
[0231] Yield: 1.26 g (94%, 4.19 mmol). 1 H-NMR (CDCl 3 )δppm: 1.79-1.90(m, 2...
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