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Just beginning to grasp this. Betaphenylethylamine to n-methyl-b-pea. Can I use water instead of DMSOesque solvent in regards to cesium carbonate/hydroxide monohydrate? Also are molecular sieves necessary? As well as 1-bromobutane?

Bottle + water + pea + cesium carbonate/hydroxide = NMPEA?

Jacob Harmon
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Your phenethylamine and bromobutane/methyl iodide are not going to be soluble in water but will dissolve in each other and react. If you use aq base and stir, possibly with gentle heating for bromobutane, then you will get your product. No need for sieves or drying agents. This is essentially a phase-transfer reaction but without a second solvent. As with any attempted amine alkylation, the danger is over reaction to give the quat. salt. If you find over reaction to be a significant problem then consider reductive amination.

Waylander
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  • Water for the solvent... and then heating and stirring to replace the need for bromobutane? I appreciate your initial response sir! – Jacob Harmon May 14 '18 at 13:56
  • You'll still need haloalkane (MeI or BuBr) or there's nothing for the phenethylamine to react with. Water for solvents as the two reactants dissolve in each other, the initial product (which will be a salt) goes into aq phase where it is neutralised, then returns to the organic phase. – Waylander May 14 '18 at 14:00
  • A little over my head. Cesium hydroxide monohydrate or cesium carbonate + phenylethylamine in a water base devoid of anything else besides stirring and heating? One pot / shake and bake style betamethylphenylethylamine? Forgive my crude explanation, all due respect to the professional chemist. – Jacob Harmon May 14 '18 at 16:04
  • Phenylethylamine + cesium hydroxide or carbonate in water does nothing. If you want N-methylphenylethylamine then you must introduce a source of that methyl. Methyl iodide will do fine. – Waylander May 14 '18 at 16:47
  • Well appreciated. Hope to apply in the near future. – Jacob Harmon May 15 '18 at 11:14
  • If this doesn't work, consider using acetonitrile and potassium carbonate – Waylander May 15 '18 at 13:11