Isopropanol → N-Butylaniline

N-butylaniline (6a) Was synthesized in an analogous manner previously reported (Org Lett, 4, 581).11 Briefly, CuI (19 mg, 0.1 mmol) and freshly ground K3PO4 (849 mg, 4 mmol) were placed in a sealed tube followed by sequential addition of isopropanol (2 mL), ethylene glycol (0.222 mL, 4.0 mL), phenyl-iodide (0.224 mL, 2.0 mmol) and n-butylamine (0.237 mL, 2.4 mmol). The tube was then sealed and stirring commenced at 80° C. for 18 h. After cooling to room temperature the reaction was diluted with water:ethyl ether (1:1, 10 mL). The aqueous layer was extracted with ether (3×5 mL), washed with brine (15 mL), dried over sodium sulfate and concentrated in vacuo. Purification via flash chromatography afforded the title compound as a yellow oil (235 mg, 79%). 1H NMR (400 MHz, CDCl3) δ 7.19 (m, 2H), 6.70 (t, J=7.2 Hz, 1H), 6.61 (d, J=8.4 Hz, 2H), 3.60 (br, 1H), 3.12 (t, J=7.2 Hz, 2H), 1.62 (m, 2H), 1.44 (m, 2H), 0.98 (t, J=7.2 Hz, 3H). Spectra matches that reported in Okano et al., “Synthesis of secondary arylamines through copper-mediated intermolecular aryl amination,” Org Lett 2003, 5(26):4987-4990.

1. customThe tube was then sealed
2. extractionThe aqueous layer was extracted with ether (3×5 mL)
3. washwashed with brine (15 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customPurification via flash chromatography

ORD record

ord-7ba4a8848b7c4a63a60a8b26fb81ef84

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409858B2