1-(2-methoxypheny1)-4-[3-(naphthalene-1-oxy)-2-hydroxypropyl] piperazine optical isomer and salt thereof, preparation method and application
A technology of methoxyphenyl and methoxyphenyl, applied in salts of optical isomers, optical isomers of 1--4-[3--2-hydroxypropyl]piperazine, and applications in medicine field, can solve the problems of no receptor subtype selectivity, reflex tachycardia, etc., and achieve the effect of high selectivity and small side effects
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0038] Dissolve 0.97g (0.04mol) of sodium hydride in 60ml of DMF (thionyl chloride), and add dropwise 20mL of a DMF solution containing 4.32g (0.03mol) of 1-naphthol, and (2R)- Tosylglycidyl 6.84g (0.03mol, 91% ee) DMF solution 20mL, room temperature reaction for 6 hours, add water 80mL to stop the reaction, extract 3 times, each time with ethyl acetate 100mL, wash the organic layer 3 times , with saturated saline 100mL each time, anhydrous Na 2 SO 4 After drying, the solvent was recovered to obtain 13.45 g of a brown oily crude product. The crude product was purified by silica gel column chromatography using petroleum ether-ethyl acetate at a volume ratio of 30:1 as the eluent to obtain 4.98 g of the product with a yield of 83% and 92% ee. Detected MSm / z(M+H + ) 201, bp118~122°C (0.25mm), it was confirmed by HPLC and standard comparison that it was (2R)-(1-naphthyloxy)-methyloxirane represented by the above formula (1).
[0039] Dissolve 26.5g (0.25mol) of diethanolamine ...
Embodiment 2
[0043] Replace (2R)-p-toluenesulfonyl glycidyl ester with (2S)-p-toluenesulfonyl glycidyl ester, and the rest of the operations are the same as in Example 1 to prepare (2S)-(1-naphthyloxy)-methyloxirane alkyl. Replace (2R)-(1-naphthyloxy)-methyl oxirane with (2S)-(1-naphthyloxy)-methyl oxirane, and the rest of the operations are the same as in Example 1 to prepare (2S) -1-(2-methoxyphenyl)-4-[3-(naphthalene-1-oxyl)-2-hydroxypropyl]piperazine, MSm / z (M+H + )393, mp.124~126°C, through HPLC and (2R)-1-(2-methoxyphenyl)-4-[3-(naphthalene-1-oxyl)-2-hydroxypropyl]piper The azine was comparatively identified as (2S)-1-(2-methoxyphenyl)-4-[3-(naphthalene-1-oxyl)-2-hydroxypropyl]piperazine.
Embodiment 3
[0045] Dissolve 50 g (0.348 mol) of 1-naphthol in 350 mL of absolute ethanol, add 15.2 g (0.38 mol) of sodium hydroxide under stirring, slowly add 96.4 g (1.044 mol) of racemic epichlorohydrin dropwise, and react at room temperature for 10 After 1 hour, the ethanol was distilled off under reduced pressure, and the residue was added with 150 mL of water, and extracted 3 times, each time using CHCl 3 50mL, combined the extracts, washed the organic phase with 5% sodium hydroxide solution, dried over anhydrous sodium sulfate, recovered the solvent, distilled the crude product under reduced pressure, collected fractions at 160~165℃ / 266Pa, and obtained 60g of viscous colorless oily liquid , yield 86.2%. Detected MSm / z(M+H + ) 201, bp 118-122°C (0.25mm), it was confirmed that the above formula (2) represented (1-naphthyloxy)-methyloxirane.
[0046] The method of Example 1 was used to obtain 9.6 g of 1-(2-methoxyphenyl)piperazine.
[0047] Dissolve 53 mg (0.88 mmol) of (S, S)-salen...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com