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29th August 2013 @ 14:57

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Reaction information

*#Reaction file  
Scheme_309.cdx
*Reaction file type CDX
*Procedure  

Benzenesulfonate (307, 7.4 g, 27.8 mmol) was added to vigorously stirring benzylamine (50.0 mL, 0.46 mol).  Catalytic iodine (200 mg, 0.27 mmol) was added and the reactants refluxed for 18 hrs, excess was benzylamine was removed by distillation (15 mm, 89 °C), and the reaction was quenched by addition of a saturated solution of NaHCO3 (30.0 mL).  The product was extracted into diethyl ether (3 x 100 mL), the combined organic layers washed with water (3 x 100 mL), brine (50.0 mL) and dried over MgSO4, filtered and the solvent removed under reduced pressure.  Kugelrohr distillation (110 °C, 1.0 mm) afforded the title product as a clear oil (5.13 g, 25.5 mmol, 91 %).

*Yield (%)  91
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp103.pdf
DM Thesis_2000_pp40-49.pdf
Further information  

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Overall reaction? True
For overall reaction - links to child reaction steps  
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Attached Files
Scheme_309.cdx
DM Thesis_2000_pp103.pdf
DM Thesis_2000_pp40-49.pdf