Aniline → N,N-Di(6-hydroxyhexyl)aniline

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A mixture of 9.3 g (100 mmol) freshly distilled aniline, 30.0 g (220 mmol) 6-chloro-1-hexanol and 30.4 g (220 mmol) potassium carbonate were heated in 50 ml of n-butanol under reflux for 4 days. After cooling the solids were filtered of and the solvent is removed in vacuum. Purification by liquid chromatography (ethyl acetate/hexane 2:1) afforded 17.6 g (60%) of a colorless oil.1 H-NMR (400 MHz, CDCl3): δ=7.18 (m, 2H), 6.61 (m, 3H), 3.91 (t, J=6.4 Hz, 4H), 3.67 (t, J=6.4 Hz, 4H), 1.90–1.77 (m, 4H), 1.70–1.53 (m, 4H), 1.50–1.31 (m, 8H). 13C-NMR (100 MHz, CDCl3); 148.19, 129.31, 115.33, 111.86, 62.793, 51.06, 32.78, 27.30, 27.05, 25.76. EI-MS: 293 (M+), 206 (M+-C5H10OH), 120 (M+-2 C5H10OH). Calcd for C18H31NO2: C, 79.67; H, 10.65; N, 4.77; O, 10.90

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