6,6-dimethylpiperidin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The oxime of 2,2 dimethylcyclopentanone is prepared by reaction of the ketone with hydroxylamine hydrochloride in EtOH, and treated with p-toluenesulfonyl chloride and DMAP. Heating then effects Beckmann rearrangement to give 6,6-dimethyl-2-piperidinone which is deprotonated with NaH in DMF solution. Reaction with n-butyl iodide then gives the title compound. Heating

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The oxime of 2,2 dimethylcyclopentanone is prepared by reaction of the ketone with hydroxylamine hydrochloride in EtOH, and treated with p-toluenesulfonyl chloride and DMAP. Heating then effects Beckmann rearrangement to give 6,6-dimethyl-2-piperidinone which is deprotonated with NaH in DMF solution. Reaction with n-butyl iodide then gives the title compound. Heating

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The oxime of 2,2 dimethylcyclopentanone is prepared by reaction of the ketone with hydroxylamine hydrochloride in EtOH, and treated with p-toluenesulfonyl chloride and DMAP. Heating then effects Beckmann rearrangement to give 6,6-dimethyl-2-piperidinone which is deprotonated with NaH in DMF solution. Reaction with n-butyl iodide then gives the title compound. Heating

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the reaction mixture was stirred at room temperature overnight The reaction mixture was quenched with 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of a 3 to 1 mixture of 3,3-dimethylpiperidin-2-one and 6,6-dimethylpiperidine-2-one (4.72 g, 37.1 mmol) in 60 ml of THF was added 60% sodium hydride suspension (1.93g, 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. the reaction mixture was stirred at room temperature overnight The reaction mixture was quenched with 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The oxime of 2,2 dimethylcyclopentanone is prepared by reaction of the ketone with hydroxylamine hydrochloride in EtOH, and treated with p-toluenesulfonyl chloride and DMAP. Heating then effects Beckmann rearrangement to give 6,6-dimethyl-2-piperidinone which is deprotonated with NaH in DMF solution. Reaction with n-butyl iodide then gives the title compound. Heating