3-(1H-IMIDAZOL-4-YL)-PIPERIDINE synthesis

5synthesis methods

Product Name:3-(1H-IMIDAZOL-4-YL)-PIPERIDINE
CAS Number:784080-46-2
Molecular formula:C8H13N3
Molecular Weight:151.21

1-Piperidinecarboxylic acid, 3-(1H-imidazol-5-yl)-, phenylmethyl ester

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784080-46-2
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Yield:784080-46-2 31%

Reaction Conditions:

Stage #1: benzyl 3-(1H-imidazol-5-yl)piperidine-1-carboxylatewith hydrogenchloride in 1,4-dioxane;water at 80; for 16 h;
Stage #2: with sodium hydrogencarbonate in water;

Steps:

21.2

Step 2. 3-(1H-Imidazol-5-yl)piperidine; 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%).

References:

US8080566,2011,B1 Location in patent:Page/Page column 51

201478-72-0 Synthesis