1,4-Dibromobutane → [4-(1-Adamantyloxy)-2,6-dimethylphenyl]pyrrolidine

Participants

Reaction Steps

A mixture of 1.8 g (6.63 mmoles) of 4-(1-adamantyloxy)-2,6-dimethylaniline, 1.43 g (6.63 mmoles) of 1,4-dibromobutane, and 2.01 g (14.6 mmoles) of K2CO3 in 25 deaerated absolute ethanol is refluxed for 45 hours, cooled, and evaporated. The residue is taken up in CH2Cl2 (125 ml) and water (125 ml). The CH2Cl2 layer is washed with water, and the combined aqueous layers are extracted with CH2Cl2 (50 ml.). The combined organic layers are dried and concentrated to give 2.4 g of a brown oil, which is chromatographed by HPLC on a 2.54 cm×109 cm column at 40 psi eluting with 0.5% acetone in CH2Cl2 and then 0.75% acetone in CH2Cl2 to give 0.45 g in the first liter eluted from the column. This solid in 1 ml of CH2Cl2 and 5 ml of ether is treated with 3.5 N HCl in ether. The hydrochloride is filtered, washed with ether, and dried to give 0.38 g of white solid, m.p. 184.4-185.6 (dec.).

Provenance & Evidence