ChemicalBook CAS DataBase List (+)-Tianeptine

(+)-Tianeptine synthesis

5synthesis methods

Product Name:(+)-Tianeptine
CAS Number:169293-31-6
Molecular formula:C21H25ClN2O4S
Molecular Weight:436.95

1231718-21-0
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Yield:-

Reaction Conditions:

Stage #1: 7-(((11RS)-3-chloro-6-methyl-6,11-dihydro-dibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanenitrile S,S-dioxidewith hydrogenchloride in water;Reflux;
Stage #2: with sodium hydroxide in water at 0 - 5; pH=~ 5.8 - 6.2;

Steps:

4

Example 4 Tianeptine Free AcidTo the crude obtained in example 3, charge cone. HCI (635 ml) to the reaction, Reflux for 18-20 hours and upon the completion of the reaction, cool the reaction mass to 0-5 ⁰C adjust the pH of the reaction mass to ~5.8 to 6.2 using 50% NaOH solution. Once the pH is adjusted cool the reaction mass to 0-5 °C, Stir the reaction at 0-5 ⁰C for 2-3 h, Filter the solids obtained, Extract the aqueous mother liquors with ethyl acetate (3^*200 ml). Dry the organic layer with sodium sulfate and distill off the solvent. Combine the solid filtered and the residue obtained, Charge toluene (150 ml) to the combined solids, Heat the reaction mass to 50-60 ⁰C, Stir the mass at 50-60 ⁰C for 2-3 h, Cool the reaction to 0-5 °C for 2-4 h and filter the solids obtained to get a pure solid.

References:

WO2010/70667,2010,A2 Location in patent:Page/Page column 5

3-Chloro-6-methyl-dibenzo[c,f][1,2]thiazepin-11(6H)-one 5,5-dioxide

26638-53-9
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169293-31-6
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References

1117-66-4
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$634.00/5g

169293-31-6
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References

26723-60-4 Synthesis

3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-ol 5,5-dioxide

26723-60-4
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References

3,11-Dichloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepine 5,5-dioxide

26638-66-4
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References