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2nd September 2013 @ 13:08

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Reaction information

*#Reaction file  
Scheme_445.cdx
*Reaction file type CDX
*Procedure  

N-Methyl-N-[(E)-3-phenyl-2-propenyl]amine (396 mg, 2.0 mmol) was added dropwise to a stirred solution of benzenesulphonate (306, 608 mg, 2.0 mmol) in MeCN (20.0 mL) and K2CO3 (2.3 g, 18 mmol), and heated at 70 °C for 14 hours.  The product was extracted into diethyl ether (3 x 50 mL), the combined layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-50 % Et2O:petroleum including 5 % Et3N) afforded the title product as a pale yellow oil (362 mg, 1.7 mmol, 85 %).

*Yield (%)  85
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp160.pdf
DM Thesis_2000_pp70-75.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
DM Thesis_2000_pp70-75.pdf
Scheme_445.cdx
DM Thesis_2000_pp160.pdf