Ethanol → HCID 15572524, compound

Temperature

0 °C

32 g of 1-carbethoxy-piperazine and 24.5 g of allyl bromide are dissolved in 70 ml of ethanol. 25 g of calcined potassium carbonate are added to the solution and the mixture is stirred under reflux for 30 hours. The reaction mixture is cooled to 0° C, the solids are filtered off, and the filtrate is evaporated under reduced pressure. The residue is admixed with 55 ml of concentrated hydrochloric acid, the mixture is boiled for 24 hours and then it is evaporated. The residue is triturated with 30 ml of ethanol and the solid is filtered off. The obtained 27 g of solid 1-allyl-piperazine dihydrochloride are dissolved in 80 ml of water, the aqueous solution is rendered alkaline (pH = 8) with 20% aqueous sodium hydroxide solution, and the alkaline mixture is extracted with 3×80 ml of ethyl ether. The etheral extracts are combined, dried over sodium sulfate, filtered, and the ether is evaporated. The resulting 15.5 g of 1-allyl-piperazine are dissolved in 100 ml of ethanol, 12.3 g of trimethylene chlorohydrine and 18 g of calcined potassium carbonate are added to the solution, and the mixture is stirred and refluxed for 30 hours. The reaction mixture is cooled to 0° C, the solids are filtered off, and the filtrate is evaporated. The obtained residue is purified by distillation. In this way 15 g (45%) of 3-(4-allyl-piperazin-1-yl)-1-hydroxy-propane are obtained; b.p.: 98°-100° C/8 mm Hg; nD20 : 1.4935.

1. temperatureunder reflux for 30 hours
2. filtrationthe solids are filtered off
3. customthe filtrate is evaporated under reduced pressure
4. customit is evaporated
5. customThe residue is triturated with 30 ml of ethanol
6. filtrationthe solid is filtered off
7. dissolutionThe obtained 27 g of solid 1-allyl-piperazine dihydrochloride are dissolved in 80 ml of water
8. extractionthe alkaline mixture is extracted with 3×80 ml of ethyl ether
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. customthe ether is evaporated
12. dissolutionThe resulting 15.5 g of 1-allyl-piperazine are dissolved in 100 ml of ethanol
13. addition12.3 g of trimethylene chlorohydrine and 18 g of calcined potassium carbonate are added to the solution
14. stirringthe mixture is stirred
15. temperaturerefluxed for 30 hours
16. temperatureThe reaction mixture is cooled to 0° C
17. filtrationthe solids are filtered off
18. customthe filtrate is evaporated
19. distillationThe obtained residue is purified by distillation

ORD record

ord-4d2c9e11a50643c28fc10d6515578888

Source dataset

uspto-grants-1979_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04140790