Hydrochloric Acid → HCID 178442829, compound

150 ml of ethanol, 6.5 g (32.8 mmol) of 1-tridecanal and 0.9 ml of concentrated hydrochloric acid were added to 5.0 g (22.0 mmol) of N1-benzyl-biguanide hydrochloride. The mixture was refluxed for 17 hours, and concentrated under reduced pressure to remove the solvent. The residue was dissolved in 100 ml of ethanol, and the solution was added to 50 ml of water and 10 ml of 5N aqueous sodium hydroxide. The mixture was refluxed for 2 hours, and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, and the extract was washed with water. After addition of 5 ml of concentrated hydrochloric acid, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution with a mixture of chloroform and methanol (9:1.5)), and further recrystallized from 80% aqueous ethanol to obtain 1.2 g of colorless crystals having a melting point of 168 to 170° C.

1. temperatureThe mixture was refluxed for 17 hours
2. concentrationconcentrated under reduced pressure
3. customto remove the solvent
4. dissolutionThe residue was dissolved in 100 ml of ethanol
5. additionthe solution was added to 50 ml of water and 10 ml of 5N aqueous sodium hydroxide
6. temperatureThe mixture was refluxed for 2 hours
7. distillationthe solvent was distilled off under reduced pressure
8. extractionThe residue was extracted with ethyl acetate
9. washthe extract was washed with water
10. additionAfter addition of 5 ml of concentrated hydrochloric acid
11. distillationthe solvent was distilled off under reduced pressure
12. customThe residue was purified by silica gel column chromatography (
13. washelution
14. additionwith a mixture of chloroform and methanol (9:1.5)), and
15. customfurther recrystallized from 80% aqueous ethanol

ORD record

ord-3d02b0603ce842229dd78dd29568b7f5

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622469B2