Sodium Hydroxide → Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate

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Reaction Steps

After adding N,N-dimethylaminopropionic acid hydrochloride (1.46 g), triethylamine (1.45 ml), 1-hydroxybenzotriazole (1.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.19 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (1.9 g) in N,N-dimethylformamide (30 ml), the mixture was stirred for 27.5 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (200 ml), brine (50 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and then washed with 1N aqueous sodium hydroxide and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (2.96 g, quantitative) as pale yellow crystals.

Provenance & Evidence