Methanol → 3-(1H-Imidazol-5-yl)piperidine

Temperature

80 °C

A 100-mL round-bottomed flask was charged with a solution of benzyl 3-(1H-imidazol-5-yl)piperidine-1-carboxylate (3 g, 10.53 mmol, 1.00 equiv) in 1,4-dioxane (30 mL) and conc. HCl (18 mL). The resulting mixture was heated to 80° C. in an oil bath for 16 hours. The reaction progress was monitored by TLC (DCM: MeOH=10:1). Upon completion, the resulting mixture was concentrated on a rotary evaporator. The resulting solution was diluted with water (60 mL) and treated with aqueous NaHCO3. The resulting mixture was then extracted with dichloromethane (4×40 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator affording 3-(1H-imidazol-5-yl)piperidine as brown oil (0.5 g, 31%).

1. concentrationUpon completion, the resulting mixture was concentrated on a rotary evaporator
2. additionThe resulting solution was diluted with water (60 mL)
3. additiontreated with aqueous NaHCO3
4. extractionThe resulting mixture was then extracted with dichloromethane (4×40 mL)
5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
6. filtrationfiltered off
7. concentrationconcentrated on a rotary evaporator

ORD record

ord-c7b993bf93b54b4b874efdca1c8e03fb

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080566B1