ChemicalBook CAS DataBase List Papaverine hydrochloride

Papaverine hydrochloride synthesis

6synthesis methods

Product Name:Papaverine hydrochloride
CAS Number:61-25-6
Molecular formula:C20H22ClNO4
Molecular Weight:375.85

1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxyisoquinolinium chloride

5884-22-0
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61-25-6
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Yield:61-25-6 89.1%

Reaction Conditions:

Stage #1:1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride with sodium hydroxide in water
Stage #2: in tetralin at 175;
Stage #3: with hydrogenchloride in methanol;water

Steps:

1.2; 2.2; 3.2
(2) Dissolve the 6,7,3',4'-tetramethoxy-1-benzyl-dihydro-isoquinoline hydrochloride (average water content: 8-15%) obtained in the previous step in 600 mL In hot waterAdd concentrated sodium hydroxide solution to make the solution phenolphthalein indicator alkaline,Filter out the precipitated 6,7,3',4'-tetramethoxy-1-benzyl-dihydro-isoquinoline (substance C), and carefully wash with water to remove sodium hydroxide;Dissolve the wet product in 330gTetrahydronaphthalene and 85g phenylethyl ether, at 175Dehydrogenation reaction in the presence of 12g Raney nickel catalyst;After the dehydrogenation is complete,The tetralin reaction mixture is filtered directly from the Raney nickel catalyst to20% hydrochloric acid aqueous solution and methanol 1:1 mixture; filter out the precipitate,In an inert gas environment (nitrogen) from ethanol-water-isobutanol solution (1:1:0.3)Medium-recrystallized, almost white6,7,3',4'-Tetramethoxy-1-benzylisoquinoline hydrochloride(Ie papaverine hydrochloride) (the yield of this step is 89.1%).

References:

Shan Northeast Da High-tech Huatai Pharmaceutical Co., Ltd.;Zhang Genglun;Zhou Hongjuan;Zhang Shuang;Xia Xiaoli CN111848512, 2020, A Location in patent:Paragraph 0251; 0253-0255; 0257-0258; 0259; 0261-0262

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58-74-2 Synthesis