Hydrochloric Acid → 5-Dimethylaminomethyl-spiro[2.5]octan-6-one

Participants

Reaction Steps

Stir a mixture of spiro[2.5]octan-6-one (252 mg, 2.03 mmol), (HCHO)n (61 mg, 2.03 mmol), dimethylamine hydrochloride (166 mg, 2.03 mmol) and 0.3 mL of conc. HCl in MeCN (30 mL) at 60° C. for 6 hours. Quench the reaction with saturated aqueous NH4Cl solution (15 mL). Basify the aqueous solution with K2CO3 to pH=9. Extract the aqueous mixture with EtOAc (30 mL×2). The combined organic layers are washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purify the residue by silica gel chromatography (CH2Cl2:MeOH=30:1) to afford 5-Dimethylaminomethyl-spiro[2.5]octan-6-one as brown oil (142 mg, yield: 38.4%). MS (m/z): 182 (M+1).

Provenance & Evidence