Methyl iodide → 1,6,6-Trimethyl-piperidin-2-one

To a solution of a 3 to 1 mixture of 3,3-dimethylpiperidin-2-one and 6,6-dimethylpiperidin-2-one (4.72 g, 37.1 mmol) in 60 ml of THF was added 60% sodium hydride suspension (1.93 g, 48.2 mmol). The grey reaction mixture was stirred at room temperature for 30 minutes. Then methyl iodide (3.02 ml, 48.2 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, and worked up with ethyl acetate/water. The orange oil was chromatographed over a prepacked 70 g silica column After elution with a 50% to 100% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 2.46 g (47%) of the title compound as a light yellow solid; and 0.91 g (17%) of isomeric 1,3,3-trimethyl-piperidin-2-one as a yellow oil.

1. stirringthe reaction mixture was stirred at room temperature overnight
2. customThe reaction mixture was quenched with water
3. customThe orange oil was chromatographed over a prepacked 70 g silica column
4. washAfter elution with a 50% to 100% ethyl acetate in heptane gradient
5. additionthe fractions containing the desired product
6. customwere collected

ORD record

ord-9bc3fdde0f144ef6b26f352c0ca4a8ae

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957213B2