Methylamine → Methyl-(4-methyl-thiazol-2-ylmethyl)-amine dihydrochloride

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Reaction Steps

Ti(OiPR)4 (1.3 eq) was added with stirring to MeNH2 (2.0 M in MeOH, 3 eq) at 0° C. under Ar. After 15 min. 4-methylthiazole-2-carbaldehyde (1 eq) was added, and the solution was stirred for 2-3 h. NaBH4 (1.4 eq, in batches if large scale) was added and stirred at 0° C. to RT overnight, followed by solvent removal in vacuo. The residue was diluted with water/CH2Cl2, and a white ppt formed. The mixture was then filtered through Celite to remove the white ppt and the layers were separated. The aqueous layer was extracted with CH2Cl2 (×3) and the combined organics were dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo to give the crude product. Purification via column chromatography yielded the pure product in 80-90% yield.

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