Triphenylphosphine → [2,2-Dimethyl-3-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-propyl]-dimethyl-amine

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A suspension of 114 mg (0.5 mmol) of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol, product of example 2, 71 mg (0.53 mmol) of 3-dimethylamino-2,2-dimethyl-1-propanol, 196.7 mg (0.75 mmol) of triphenyl phosphine in THF (4 ml) was treated at RT with 123 μl (0.75 mmol) of diethyl azodicarboxylate and stirred at RT for 48 h. The precipitate that had formed was removed by filtration, the filtrate was concentrated in vacuo and the oily residue obtained was applied to silica gel column with CH2Cl2/MeOH/NH4OH (90:10:1) as eluent. The purified fractions were combined and concentrated in vacuo. The residue was taken up in ether, the crystalline solid that formed was filtered off by suction and dried in a high vacuum to give 24 mg (23%) of the desired [2,2-dimethyl-3-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-propyl]-dimethyl-amine as an off-white solid. ISP mass spectrum, m/e: 342.4 (M+1 calculated for C21H31N3O: 342). (Further material, 30 mg, 29%, was obtained on concentration of the mother liquid and collection of the product as hydrochloride salt).

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