HCID 13478150, compound → 4-(2-Methoxy-1,1-dimethylethyl)piperidine

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Reaction Steps

A solution of 4-(1,1-dimethyl-2-methoxyethyl)pyridine (10.0 g) in acetic acid (120 ml) was catalytically hydrogenated over platinum dioxide at 40 p.s.i. for 41 hours at from ambient temperature to 43° C. After 24 hours a further quantity of platinum dioxide was added, and a final addition was made after a further 8 hours. After a total of 41 hours the solution obtained after filtration of the catalyst was evaporated in vacuo and further evaporated after the addition of toluene to remove acetic acid. The resultant yellow oil was dissolved in dichloromethane and brought to pH12 with dilute aqueous sodium hydroxide solution. After saturation with sodium chloride, the organic phase was separated and the aqueous layer was re-extracted with five portions of dichloromethane. The combined organic solution was dried over anhydrous magnesium sulphate, and evaporated in vacuo to give 4-(1,1-dimethyl-2-methoxyethyl)piperidine (9.7 g) as a straw-coloured oil.

Provenance & Evidence