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29th August 2013 @ 14:52

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Reaction information

*#Reaction file  
Scheme_305.cdx
*Reaction file type CDX
*Procedure  

To a pre-dried sealed tube, with a screw down Young tap, methylamine (66 % solution in IMS, 27.2 mL, 544 mmol) was added followed by 4-bromo-1-butene (20.0 g, 136.0 mmol).  The tube was sealed, heated to 80 °C in an oil bath for 48 hours, the reaction mixture cooled to 0 °C, then quenched with a saturated solution of NaHCO3 (50.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  The product was purified by distillation through a Dufton column at atmospheric pressure (B.p. 80-82 °C) to afford N-(3-butenyl)-N-methylamine (2.50 g, 29 mmol, 21 %) as a colourless oil.  N,N-di(3-butenyl)-N-methylamine (305) was isolated by distillation at atmospheric pressure (B.p. 120-122°C) as a colourless oil (4.8 g, 34 mmol, 51 %).  

*Yield (%)  21, 51
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp99.pdf
DM Thesis_2000_pp40-49.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
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Attached Files
Scheme_305.cdx
DM Thesis_2000_pp99.pdf
DM Thesis_2000_pp40-49.pdf