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29th August 2013 @ 15:04

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Reaction information

*#Reaction file  
Scheme_312.cdx
*Reaction file type CDX
*Procedure  

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
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp106.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
Scheme_312.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp106.pdf