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2nd September 2013 @ 13:17

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Reaction information

*#Reaction file  
Scheme_556.cdx
Scheme_560.cdx
*Reaction file type CDX
*Procedure  To a stirred solution of methylamine (66 % solution in IMS, 30.0 mL, 787 mmol), cinnamyl bromide (30.0 g, 197.0 mmol) was added at 0 °C, warmed to room temperature and refluxed for 2 hours.  The reaction was quenched with a saturated solution of NaHCO3 (30.0 mL).  The products extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried with MgSO4, filtered an the solvent removed under reduced pressure.  Kugelrohr distillation afforded the desired secondary amine (556, 135 °C, 9 mm Hg, 21.55 g, 145 mmol, 76 %) as a colourless oil and the bis tertiary amine (560, 165 °C, 5 mm Hg, 9.75 g, 40.0 mmol, 20 %) as a viscous oil. 
*Yield (%)  76, 20
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp169.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_556.cdx
DM Thesis_2000_pp169.pdf
DM Thesis_2000_pp81-89.pdf
Scheme_560.cdx