Hydrochloric Acid → 3-Pyridinemethanamine,2-(methylamino)-(9CI)

Borane/THF complex (1.44 mol) as a 1 M solution in tetrahydrofuran was added, dropwise, to a solution of 2-(methylamino)-nicotinonitrile (63.9 g, 480 mmol) in tetrahydrofuran (480 mL). This mixture was stirred at room temperature for 1 hour then heated to reflux for 3 hours. The reaction mixture was quenched by dropwise addition of methanol (136 mL, 3.36 mol) followed by 6M HCl (80 mol, 480 mmol) and 10% HCl (400 mL). The phases were separated and the organic phase washed with brine (2×480 mL). The aqueous phase was made alkaline with 50% aqueous NaOH (250 g). The aqueous phase was extracted with dichloromethane (2×480 mL) and the organic extracts dried over Na2SO4. Concentration in vacuo gave 44.85 g of 3-(aminomethyl)-2-methylaminopyridine as a pale yellow oil.

1. temperaturethen heated
2. temperatureto reflux for 3 hours
3. customThe phases were separated
4. washthe organic phase washed with brine (2×480 mL)
5. extractionThe aqueous phase was extracted with dichloromethane (2×480 mL)
6. dry with materialthe organic extracts dried over Na2SO4
7. concentrationConcentration in vacuo

ORD record

ord-b61d264713764979a4b195b478b55c87

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05002944