Water → HCID 23295884, compound

This example illustrates a synthesis of N-(10,11-Oxidoundecyl)-2-piperidone (inventive compound no. 1618). A mixture of potassium hydroxide (1.55 g, 25 mmol, pellets ground in mortar and pestle) and tetrabutylammonium bromide (1.61 g, 5.0 mmol) was stirred in dry tetrahydrofuran (10 mL). A solution of d-valerolactam (2.5 g, 25 mmol) and 1-bromo-10-undecene (Lancaster, 5.9 g, 25 mmol) in tetrahydrofuran (15 mL) was added by syringe pump over 1 hour. After stirring for a further 6 hours. Water (60 mL) and dichloromethane (60 mL) was added to the reaction mixture. The layers were separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with water (50 mL) and saturated salt solution (50 mL) and then dried with sodium sulfate. The residue was further purified by chromatography using silica and 30% hexane, ethyl acetate to yield 2.88 g (46% yield) of N-(10-Undecenyl)-2-piperidone (inventive compound no. 1616) as a colorless oil.

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
3. washThe combined organic layers were washed with water (50 mL) and saturated salt solution (50 mL)
4. dry with materialdried with sodium sulfate
5. customThe residue was further purified by chromatography

ORD record

ord-cabbea8822fa4bbda5df20dbc2dd5566

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866576