Water → 2-Phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

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Reaction Steps

Combine 2-iminopiperidine hydrochloride (4.9 g, 36.4 mmol, 3 equiv) and 2-bromoacetophenone (2.4 g, 12.1 mmol) with Na2CO3 (5.1 g, 48.4 mmol) in dry DMF (15 mL) and heat the mixture at 80° C. for 16 hours. Then, cool the mixture to room temperature, add water (200 mL), and extract with ether (3×100 mL). Wash the combined organic layers with water (2×50 mL), and re-extract the aqueous layer with ether (2×50 mL). Wash the combined organic layers with saturated aqueous sodium chloride (100 mL), dry (MgSO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2; eluent: CH2Cl2 to CH2Cl2:MeOH 50:1) to obtain a brown solid, 1.7 g, 71% yield. MS(ES+): m/z=199.1 (M+H)+

Provenance & Evidence