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2nd September 2013 @ 13:22

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Reaction information

*#Reaction file  
Scheme_561.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of N-methyl-N-[(E)-3-phenyl-2-propenyl]amine (556, 372 mg, 2.0 mmol), propargyl bromide (260 mg, 2.2 mmol) was added dropwise at 0 °C.  The mixture was then heated to 34 °C for 5 minutes before quenching with a saturated solution of NaHCO3 (15.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), filtered and the solvent removed under reduced pressure.  Additional propargyl bromide (260 mg, 2.2 mmol) was added to the crude product and the procedure repeated before quenching the reaction with a saturated solution of NaHCO3 (15.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 30 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 pale oil (264 g, 1.4 mmol, 73 %). 

*Yield (%)  73
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp172.pdf
DM Thesis_2000_pp81-89.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_561.cdx
DM Thesis_2000_pp172.pdf
DM Thesis_2000_pp81-89.pdf