4-Aminophenol → 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-aminophenol (4.0 g, 37.4 mmol), 1-(2-chloroethyl)-pyrrolidine hydrochloride (7.6 g, 44.9 mmol, 1.2 equiv), NaOH (3.7 g, 93.5 mmol, 2.5 equiv) in DMF (64 mL) is stirred for 2 h at 75° C., under an argon atmosphere. The mixture is allowed to cool to RT and then filtered through a glass sintered funnel. The filtrate is diluted with CH2Cl2 (200 mL), washed with brine (2×50 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel (260 g) column chromatography (CH2Cl2/MeOH, 70/30→50/50) to afford the title compound as a dark brown oil: ES-MS: 207.1 [M+H]+; Rf=0.18 (CH2Cl2/MeOH, 50/50).

Provenance & Evidence