Methylamine → (4-Fluoro-2-methylsulfanyl-benzyl)-methyl-amine

A solution of 2-methylthio-4-fluorobenzaldehyde (2.04 g, 12 mmol) and 2M methylamine in methanol (24 mL, 48 mmol) was stirred at room temperature for 2 h. To this was added a solution of ZnCl2 (0.818 g, 6 mmol) and NaCNBH3 (0.754 g, 12 mmol) in methanol (30 mL). After stirring for 20 h, the reaction mixture was concentrated and the resulting residue was taken up in aqueous NaOH (0.5 M, 20 mL), extracted with CH2Cl2 (5×50 mL). The combined organic layers were concentrated and the resulting residue was taken up in 1N HCl (25 mL). This solution was extracted with ethyl acetate (3×25 mL). The organic layers were discarded and aqueous layer was brought to pH 9 by adding Na2CO3 and extracted with CH2Cl2 (3×50 mL). The combined CH2Cl2 layers were dried over MgSO4, filtered and concentrated to give the desired benzylamine as a viscous pale yellow oil (1.4 g, 60% pure).

1. concentrationthe reaction mixture was concentrated
2. extractionextracted with CH2Cl2 (5×50 mL)
3. concentrationThe combined organic layers were concentrated
4. extractionThis solution was extracted with ethyl acetate (3×25 mL)
5. additionby adding Na2CO3
6. extractionextracted with CH2Cl2 (3×50 mL)
7. dry with materialThe combined CH2Cl2 layers were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-ee1866a3e95b4f338ed2ffd535cfd039

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109186B2