Hydrochloric Acid → 3-Chloro-N-(3-chloropropyl)-N-methylpropan-1-amine--hydrogen chloride (1/1)

A solution of about 60 grams of N,N-bis(3-hydroxypropyl)methylamine in 110 ml of chloroform is saturated, with cooling and stirring, with anhydrous hydrogen chloride gas. To the resulting two-phase liquid mixture is added, over a period of about 30 minutes at a temperature of 0-5° C., approximately 66 ml of thionyl chloride. The homogeneous solution thus obtained is allowed to stand at room temperature for a period of about 15 hours, the solution is then heated at reflux temperature for an additional two-hour period, and the chloroform is evaporated in vacuo from the light brown-colored reaction solution. The residual material is washed with ethanol, and is then crystallized from a mixture of 200 ml ethanol: 800 ml ether. The white crystalline product thus obtained is recovered by filtration, washed with three portions of ether, then with hexane, and dried in vacuo at 25° C. to give about 80 grams of N,N-bis(3-chloropropyl) methylamine hydrochloride; m.p. 86-88° C.

1. temperaturewith cooling
2. customThe homogeneous solution thus obtained
3. temperaturethe solution is then heated
4. temperatureat reflux temperature for an additional two-hour period
5. customthe chloroform is evaporated in vacuo from the light brown-colored reaction solution
6. washThe residual material is washed with ethanol
7. customis then crystallized from a mixture of 200 ml ethanol
8. customThe white crystalline product thus obtained
9. filtrationis recovered by filtration
10. washwashed with three portions of ether
11. dry with materialwith hexane, and dried in vacuo at 25° C.

ORD record

ord-b4f378b0ae7c44f68f4a0290e52c0aa5

Source dataset

uspto-grants-1978_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04093657