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29th August 2013 @ 15:04

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Reaction information

*#Reaction file  
*Reaction file type CDX

To a stirring solution of N-benzyl-N-(3-heptynyl)amine (309, 1.0 g, 4.8 mmol), K2CO3 (1.2 g, 12.0 mmol) and MeCN (10.0 mL), benzenesulfonate (307, 1.33 g, 5.0 mmol) was added dropwise.  The reactants were refluxed for 24 hrs then quenched using NaOH (6M, 30.0 mL).  The product was extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (3 x 100 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a viscous clear oil (1.3 g, 4.4 mmol, 88 %).

*Yield (%)  88
*Type of Yield Isolated product yield
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp106.pdf
Further information  

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Overall reaction? True
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Attached Files
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp106.pdf