Triphenylphosphine → 4-(3-Chloropropyl)pyridine

3-(4-Pyridyl)-1-propanol (2.68 g, 19.3724 mmol) was dissolved in dichloromethane (100 ml), triphenylphosphine (5.6 g. 21.3096 mmol) was added, and then N-chlorosuccinimide (2.6 g, 19.3724 mmol) was gradually added while cooling on ice prior to stirring overnight. After distilling off the solvent under reduced pressure, the residue was dissolved in ethyl acetate and extracted with 1N hydrochloric acid. Upon neutralization with saturated bicarbonate water, the mixture was extracted with ethyl acetate, washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (2,375 g, 15.2605 mmol, 78.77%) as a yellowish-brown oil. This was used without further purification for the following reaction.

1. temperaturewhile cooling on ice
2. distillationAfter distilling off the solvent under reduced pressure
3. dissolutionthe residue was dissolved in ethyl acetate
4. extractionextracted with 1N hydrochloric acid
5. extractionUpon neutralization with saturated bicarbonate water, the mixture was extracted with ethyl acetate
6. washwashed with saturated saline
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-e5e88d60add44403b3c171510992fffb

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372981B2