3-Chloro-1-propanol → 3,3'-(Methylazanediyl)di(propan-1-ol)

To this aqueous N-(3-hydroxypropyl)methylamine solution is added a second 249.5 g portion of 3-chloro-1-propanol, and the resulting mixture is heated under reflux at a temperature of approximately 105° C. for a period of about 5 hours, during which time about 195 grams of a 50% aqueous sodium hydroxide solution is added slowly at a rate sufficient to maintain the pH between about 8 and 9. The reaction mixture is cooled to room temperature, filtered, and the filtered aqueous solution is extracted with three 500 ml-portions of n-butanol. The butanol extracts are combined, evaporated to a small volume in vacuo, and the residual slurry is triturated with 300 ml of ethyl ether. The resulting ethereal slurry is filtered, thereby removing insoluble inorganic solid material, and the latter is washed with 100 ml of ethyl ether. The ether solution and washings are combined, the ether is evaporated therefrom in vacuo, and the residual oil is distilled in vacuo to give about 123 grams of N,N-bis(3-hydroxypropyl)methylamine; b.p. 110° C. at 150 microns pressure.

1. temperaturethe resulting mixture is heated
2. additionis added slowly at a rate sufficient
3. temperatureto maintain the pH between about 8 and 9
4. filtrationfiltered
5. extractionthe filtered aqueous solution is extracted with three 500 ml-portions of n-butanol
6. customevaporated to a small volume in vacuo
7. customthe residual slurry is triturated with 300 ml of ethyl ether
8. filtrationThe resulting ethereal slurry is filtered
9. washremoving insoluble inorganic solid material, and the latter is washed with 100 ml of ethyl ether
10. customthe ether is evaporated
11. distillationin vacuo, and the residual oil is distilled in vacuo

ORD record

ord-61a122970a1c4c20b1d0e9de8486c847

Source dataset

uspto-grants-1978_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04093657