1-Iodooctane → 1-Octylpyridin-1-ium iodide

Temperature

80 °C

To a stirring solution of 13 (0.150 mg, 0.34 mmol) in dry CH2Cl2 (5 mL) was added dropwise 1-iodooctane (0.6 mL, 0.792 g, 3.3 mmol) at room temperature. The reaction mixture was then stirred at 80° C. under N2 for 1 day. After cooling to room temperature, the mixture was next concentrated in vacuo and washed with hexane (20 mL) to give the corresponding n-octyl-pyridinium iodide salt 14 as an analytically pure yellow solid (0.211 g, 95.4%). To a suspension of 12 (0.136 g, 0.2 mmol) in dry methanol (1 mL) was added dropwise a solution of sodium methoxide in methanol (0.5 mL, 0.5 M) at room temperature. A clear reddish solution was obtained from which an orange precipitate immediately formed. The precipitate was collected by filtration and washed with dry methanol to give analytically pure product (0.096 g, 86.8%) as a brown solid: mp>280° C.; 1H NMR (400 MHz, CD3OD): δ 8.816 (s, 2H), 7.395 (s, 2H), 7.317 (s, 2H), 7.160 (d, 1H, J=16.4 Hz), 6.841 (d, 1H, J=16.0 Hz), 4.547 (t, 2H, J=8.0 Hz), 2.146 (s, 6H), 2.065 (m, 2H), 1.912 (s, 6H), 1.450 (s, 18H), 1.307 (m, 10H), 0.895 (s, 3H); 13C NMR (100 MHz, CD3OD): δ 159.608, 154.285, 142.183, 139.217, 138.198, 136.351, 133.757, 131.838, 130.964, 128.398, 126.424, 124.704, 123.758, 61.530, 34.624, 32.031, 31.931, 30.493, 29.292, 26.399, 22.850, 20.057, 17.463, 14.352; HRMS (EI): m/z 553.4263 [M+]; calcd, 553.4284; Anal. Calcd. for C39H55NO.2H2O: C, 79.41; H, 10.08; N, 2.37. Found; C, 79.71; H, 9.63; N, 2.14.

1. temperatureAfter cooling to room temperature
2. concentrationthe mixture was next concentrated in vacuo
3. washwashed with hexane (20 mL)

ORD record

ord-c4def80ef7df4441ba228a7ca1b76bf2

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968016B2