ChemicalBook CAS DataBase List 5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE

5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE synthesis

8synthesis methods

Product Name:5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE
CAS Number:131986-45-3
Molecular formula:C14H23N3OS
Molecular Weight:281.42

131988-19-7 Synthesis

3-(4-HEXYLOXY-1,2,5-THIADIAZOL-3-YL)-1-METHYLPYRIDINIUM IODIDE

131988-19-7
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5-(4-HEXYLOXY-[1,2,5]THIADIAZOL-3-YL)-1-METHYL-1,2,3,6-TETRAHYDRO-PYRIDINE

131986-45-3
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Yield:131986-45-3 77.1%

Reaction Conditions:

with sodium tetrahydridoborate in ethanol at -5 - 0; for 1 h;

Steps:

1.6 Step 6. Preparation of Zanomeline

To the 250mL three-necked reaction flask, add Intermediate 5 (2.00g, 4.9mmol, 1.0eq),Ethanol (24.00mL) was stirred to dissolve,-5 ~ 0 NaBH4 (371mg, 9.8mmol, 2.0eq) was added dropwiseethanol (16.00mL) suspension,Stir at the same temperature for 1 hour.Add pure water (100.00mL) to quench,The aqueous phase was extracted with dichloromethane (100 mL×3).Combine the organic phases,dried over anhydrous sodium sulfate,Filter and concentrate under reduced pressure.Crude product column chromatography (dichloromethane/methanol 20:1)A tan solid was obtained (1.11 g, yield 77.1%, purity 99.99%).

References:

CN114853750,2022,A Location in patent:Paragraph 0176-0177; 0188-0190