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Pictet-Spengler route to Praziquantel
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9th May 2012 @ 01:27
START: 09/05/12
FINISH:

Background




Hazard and Risk Assessment
As for KAB26-X.

Previous Experiments
Yb(OTf)3 catalysed PS reaction to give 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB21-9)
TFA catalysed synthesis of 6,7-dimethoxy-1-(4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline (KAB24-4)
Lewis acid-catalyst screen for the PS reaction to give KAB21 and KAB24

Following Experiments

Chemical Information
2-(3,4-dimethoxyphenyl)-N-(4-nitrobenzylidene)ethanamine (KAB23-1) - SMILES: O=[N+]([O-])C1=CC=C(/C=N/CCC2=CC(OC)=C(OC)C=C2)C=C1, InChI: InChI=1S/C17H18N2O4/c1-22-16-8-5-13(11-17(16)23-2)9-10-18-12-14-3-6-15(7-4-14)19(20)21/h3-8,11-12H,9-10H2,1-2H3/b18-12-, InChIKey: LMBMXYXQVBPKHJ-PDGQHHTCSA-N.

Procedure
09/05/12. Gold(III) chloride trihydrate (13 mg, 0.033 mmol, 1 mol%) and silver triflate (17 mg, 0.066 mmol, 2 mol%) were vigorously stirred in MeCN (5 mL) for 1 hour before the addition of a solution of KAB23-1 (1.00 g, 3.181 mmol, 1 equiv.) dissolved in MeCN (90 mL). The reaction mixture was left to stir at rt from 10:45.

Summary and Conclusion

References
[1] S. W. Youn, The Journal of Organic Chemistry 2006, 71, 2521-2523. DOI: 10.1021/jo0524775. Paper


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