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30th August 2013 @ 14:18

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Reaction information

*#Reaction file  
Scheme_424.cdx
*Reaction file type CDX
*Procedure  

N-Methyl-allyl-amine (2.28 g, 30.0 mmol) was added dropwise to a stirred solution of benzenesulphonate (415, 5.58 g, 17.3 mmol) in MeCN (20.0 mL) and K2CO3 (2.3 g, 18.0 mmol), heated at 70 °C for 14 hours, the reaction quenched with a saturated solution of NaHCO3 (50.0 mL).  The product extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL) dried over MgSO4, the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-50 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a pale yellow oil (2.74 g, 13.5 mmol, 78 %).   

*Yield (%)  78
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp157.pdf
DM Thesis_2000_pp64.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_pp64.pdf
Scheme_424.cdx
DM Thesis_2000_pp157.pdf