R-tetrahydropapaverine HCl synthesis
- Product Name:R-tetrahydropapaverine HCl
- CAS Number:54417-53-7
- Molecular formula:C20H26ClNO4
- Molecular Weight:379.88
6429-04-5
54417-53-7
The general procedure for the synthesis of the target compound using 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride as raw material was as follows: 20 g of 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride was dissolved in 400 mL of distilled water, and stirred until completely dissolved. Subsequently, ammonia was added to the solution to adjust the pH, and after observing that no white oily material precipitated, 400 mL of toluene was added and mixed with thorough stirring. The organic phase (toluene layer) and the aqueous phase were separated to ensure that there was no residual raw material in the aqueous phase. The organic phase was dried with anhydrous sodium sulfate to obtain 17.3 g of racemate. The racemate was dissolved in 173 mL of acetonitrile and heated to 70 °C. 3.93 g of the splitting agent N-acetyl-D-leucine was slowly added and the reaction was stirred for 20 minutes. Next, 0.522 g of the splitting agent N-acetyl-D-phenylalanine was added and the reaction was continued with stirring for 35 minutes. Upon completion of the reaction, it was slowly cooled to room temperature and subsequently stored in a refrigerator at 4°C for 24 hours to promote crystallization. Upon completion of crystallization, the solid product was collected by filtration. The product was converted to hydrochloride form, treated by adding appropriate amount of hydrochloric acid and dried to give 8.325 g of 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride in R-configuration. The total yield was 83.25% and the purity was 97.6%.
6429-04-5
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54417-53-7
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Yield:54417-53-7 83.25%
Reaction Conditions:
with N-acetyl-D-leucine;(R)-N-acetylphenylalanin in water;toluene;acetonitrile at 4 - 70; for 24.92 h;Reagent/catalyst;
Steps:
1
20 g of tetrahydro papaverine hydrochloride was dissolved in 400 mL of distilled water,Stir to completely dissolve, add ammonia to free, no white oil precipitation,Add 400mL toluene to stir well, to the water layer without tetrahydro-papaverine,The toluene layer was dried over anhydrous sodium sulfate,And 17.3 g of tetrahydropiperidinine racemate was obtained.The tetrahydro-papaverine racemate was dissolved in 173 mL of acetonitrile, heated to 70 ° C,Slowly adding the resolving agent N-acetyl-D-leucine 3.93g, stirring reaction 20min,Adding the resolving agent N-acetyl-D-phenylalanine 0.522g, stirring reaction 35min,Slowly down to room temperature, after the refrigerator at 4 for 24 hours, waiting for crystallization.After the solid precipitated, the product was converted to the hydrochloride salt by filtration, hydrochloric acid was added,And dried to obtain 8.325 g of R-tetrahydrocaproline hydrochloride.The total yield was 83.25% and the purity was 97.6%.
References:
Harbin Medical University;Han Weina;Chai Qi;Liu Jinfeng;Fu Ran;Ren Yongfei;Shi Mingxing CN107056700, 2017, A Location in patent:Paragraph 0040-0043; 0046; 0058
50896-90-7
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54417-53-7
227 suppliers
$45.00/1g
![1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline](/CAS/GIF/6957-27-3.gif)
![(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride](/CAS/20180713/GIF/54417-52-6.gif)