Hydrochloric Acid → HCID 118162222, compound

To a round-bottomed flask was added tert-butyl ((6-methyl-4-(trifluoromethyl)pyridin-3-yl)methyl)carbamate (1.0 equiv.) which was dissolved in DCM (0.7 M). To this solution was added in-chloroperoxybenzoic acid (1.3 equiv.) and the mixture was stirred at room temperature for 12 h. The solvent was removed to afford a crude solid which was dissolved in MeOH and 4 N HCl in dioxane (4.2 equiv.) was added at room temperature. The mixture was stirred for 24 h and some precipitate begun to form. The volatile solvents were removed under reduced pressure to afford a crude residue. The residue was dissolved in methanaol and the resulting mixture was loaded on a Strata ion-exchange column. The column was washed successively with water, acetonitrile, MeOH and 7 N ammonia in MeOH. The product eluted with the 7 N ammonia in MeOH eluent and product containing eluent was concentrated under reduced pressure to afford 5-(aminomethyl)-2-methyl-4-(trifluoromethyl)pyridine 1-oxide (90% yield) as the free base; MS(ESI) m/z 207.0[M+1]+.

1. customThe solvent was removed
2. customto afford a crude solid which
3. stirringThe mixture was stirred for 24 h
4. customto form
5. customThe volatile solvents were removed under reduced pressure
6. customto afford a crude residue
7. dissolutionThe residue was dissolved in methanaol
8. washThe column was washed successively with water, acetonitrile, MeOH and 7 N ammonia in MeOH
9. washThe product eluted with the 7 N ammonia in MeOH eluent and product
10. additioncontaining eluent
11. concentrationwas concentrated under reduced pressure

ORD record

ord-2a0f407bf6574f64ba6ccc1847fa6a3b

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156798B2