SYNTHESIS OF N-(1,1-DIMETHYLETHYL)-2-METHYLPROPYLIMINE
- 2-Methylpropanal (72g, 1.0 mol) is added dropwise and with
stirring during 2 hours to 1,1-dimethylethylamine (t-butylamine) (73g 1.0
mol).
- During the addition the temperature rises from 25 to 40 °C and an aqueous
layer separates near the end of the addition.
- The organic layer is treated with
anhydrous potassium carbonate (15g), stirred at 25 °C for 17 hours, and then
decanted on to barium oxide (12g).
- After the mixture has been stirred for 10
hours, it is filtered and the organic filtrate is distilled to separate the
imine as a colourless liquid, b.p. 56°C/75mmHg, 88.3g (70%); i.r. (CCl₄)
1675cm⁻¹ (C=N); p.m.r. (CCl₄, TMS) 1.05 [d, 6H J = 7Hz, (Me)₂CH-],
1.10 [s, 9H,-C(Me)₃], 2.0-2.6 (m, 1H, CH), and 7.49 (d, 1H, J = 4.5
Hz, CH=N); m/z 127, 112, 72, 57, 56, 55, and 41.
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