Hydrochloric Acid → HCID 53950422, compound

26.5 g (0.1 mole) quantity of 11-bromoundecanoic acid was dissolved in 300 ml of methanol, and 5 to 6 drops of sulfuric acid was added thereto and the mixture was stirred at room temperature for 24 hours and concentrated. 500 ml quantity of ethyl acetate was added to the residue and the solution was washed sequentially with 100 ml of water and 100 ml of a brine, and then dried over anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure and the residue was dissolved in 200 ml of dimethylformamide. To the solution were added 11.4 g (0.1 mole) of formylpiperazine and 18.5 g (0.22 mole) of sodium hydrogencarbonate. The mixture was stirred at 80 ° C for 3 hours and concentrated under reduced pressure. 500 ml quantity of ethyl acetate was added to the residue and the mixture was washed sequentially with 100 ml of water and 100 ml of a brine, and then dried over anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure. To the residue were added 300 ml of methanol and 50 ml of concentrated hydrochloric acid, and the mixture was refluxed for 3 hours. The solvent was evaporated under reduced pressure and the precipitated white crystals were washed with acetone, giving 25 g (yield: 70 %) of 11-(1-piperazinyl)undecanoic acid methyl ester as a hydrochloride.

1. concentrationconcentrated
2. addition500 ml quantity of ethyl acetate was added to the residue
3. washthe solution was washed sequentially with 100 ml of water and 100 ml of a brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customEthyl acetate was evaporated under reduced pressure
6. dissolutionthe residue was dissolved in 200 ml of dimethylformamide
7. stirringThe mixture was stirred at 80 ° C for 3 hours
8. concentrationconcentrated under reduced pressure
9. addition500 ml quantity of ethyl acetate was added to the residue
10. washthe mixture was washed sequentially with 100 ml of water and 100 ml of a brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customEthyl acetate was evaporated under reduced pressure
13. additionTo the residue were added 300 ml of methanol and 50 ml of concentrated hydrochloric acid
14. temperaturethe mixture was refluxed for 3 hours
15. customThe solvent was evaporated under reduced pressure
16. washthe precipitated white crystals were washed with acetone

ORD record

ord-8669b1b4f6ad467ba4c3b1a6f7f1f5ce

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05318970