3-(Diethylamino)-1-propanol → 3-Chloropropyl(diethyl)amine

A solution of 3-diethylamino-1-propanol (Aldrich) (10 g, 76 mmol) in DCM was stirred at 0° C. A solution of thionyl chloride (DCM 30 mL) was then added drop-wise such that the reaction temperature remained at 0° C. Once addition is complete, the reaction was refluxed for one hour. The reaction was allowed to cool and the excess DCM and thionyl chloride were removed under vacuum. The residue was basified (pH8–9) using 2N NaOH and the aqueous mixture extracted with DCM (3×100 mL). The organic extracts were combined, dried (MgSO4) and evaporated to give a brown oil. The oil was distilled (160°–165° C.) to give the product as a clear oil (4.2 g 36.9%).

1. customremained at 0° C
2. additionOnce addition
3. temperaturethe reaction was refluxed for one hour
4. temperatureto cool
5. customthe excess DCM and thionyl chloride were removed under vacuum
6. extractionthe aqueous mixture extracted with DCM (3×100 mL)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customto give a brown oil
10. distillationThe oil was distilled (160°–165° C.)

ORD record

ord-067eb0a6da1c4fb8bb01b9174fb31c6a

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07173061B2