Cyclopropanemethanamine → Cyclopropylmethyl-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-amine

Participants

Reaction Steps

A suspension of 1.01 g (3 mmol) of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline, 0.186 g (0.3 mmol) rac BINAP, 33.7 mg (0.15 mmol) of palladium(II)acetate and 0.87 g (9 mmol) of sodium tert-butylate in toluene (25 ml) was treated at RT with 0.427 g (6 mmol) of aminomethyl cyclopropane and then heated to reflux under an argon atmosphere for 20 h. The reaction mixture was then filterd by suction over fiberglass filter paper and the filtrate was partitioned between EtOAc and water. The layers were separated, the organic layer dried over sodium sulphate and concentrated in vacuo. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (15:1:0.2) as eluent. Combination of the purified fractions and concentration in vacuo gave 253 mg (30%) of the desired cyclopropylmethyl-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-amine as light yellow foam. ISP mass spectrum, m/e: 282.2 (M+1 calculated for C18H23N3O: 282).

Provenance & Evidence