Thionyl Chloride → 1-(2-Chloroethyl)pyrrolidine hydrochloride

2-pyrrolidin-1-ylethanol (6.24 g, 0.05 mol) was stirred while cautiously adding thionyl chloride (40 mL, 0.54 mol). The stirred mixture was refluxed for 1 hour under nitrogen atmosphere, then concentrated in vacuo. The residue was triturated with diethyl ether to give a solid, and the liquid decanted; this process was repeated several times, until the decantate was almost colorless. The flask containing solid was evaporated to give a free-flowing, cocoa-colored solid (4.21 g, 46%). 1H-NMR (CD2Cl2): δ 13.1 (br s, 1 H), 3.97 (t, 3 H), 3.7 (m, 2 H), 3.33 (dd, 2 H), 2.81 (m, 2 H), 2.14-1.95 (m, 3 H).

1. temperatureThe stirred mixture was refluxed for 1 hour under nitrogen atmosphere
2. concentrationconcentrated in vacuo
3. customThe residue was triturated with diethyl ether
4. customto give a solid
5. customthe liquid decanted
6. additionThe flask containing solid
7. customwas evaporated

ORD record

ord-c3846f94479c4256a5d79d51b5c5eb97

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431695B2