2-Methyl-2-(pyridin-2-yl)propanenitrile → 2-Methyl-2-(pyridin-2-yl)propan-1-amine

To a solution of 2-methyl-2-(2-pyridyl)-propionitrile (1.018 g, 6.97 mmol) in 25 mL of anhydrous diethyl ether under a blanket of Argon was added LiAlH4 (0.538 g, 14.17 mmol) portionwise. After 1 h the reaction was quenched with the addition of water (1 mL), NaOH (1.0 mL, 1N), water (8 mL) then diethyl ether (20 mL) and let stir for 10 h. The solution was filtered through a plug of celite and washed with diethyl ether:MeOH (1:1) (200 mL). The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (30×150 mm column of SiO2, CH2Cl2 /CH2Cl2 saturated with NH3 /MeOH gradient elution 60:39:1 to 60:38:2 to 60:37:3) to give the title compound as a resin:

1. customAfter 1 h the reaction was quenched with the addition of water (1 mL), NaOH (1.0 mL, 1N), water (8 mL)
2. filtrationThe solution was filtered through a plug of celite
3. washwashed with diethyl ether:MeOH (1:1) (200 mL)
4. concentrationThe filtrate was concentrated in vacuo
5. customthe residue was purified by flash column chromatography (30×150 mm column of SiO2, CH2Cl2 /CH2Cl2 saturated with NH3 /MeOH gradient elution 60:39:1 to 60:38:2 to 60:37:3)

ORD record

ord-b37c1dd825644131aa79526f491d9101

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866573