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

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.

1. stirringstirred at 0° C. to RT overnight
2. customfollowed by solvent removal in vacuo
3. additionThe residue was diluted with water/CH2Cl2
4. customa white ppt formed
5. filtrationThe mixture was then filtered through Celite
6. customto remove the white ppt
7. customthe layers were separated
8. extractionThe aqueous layer was extracted with CH2Cl2 (×3)
9. dry with materialthe combined organics were dried over Na2SO4
10. filtrationThe inorganics were filtered off
11. customthe solvent was removed in vacuo

ORD record

ord-94b7f0e6194e43beac2fa630b1155ec6

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2