Water → HCID 18946306, compound

A mixture of 4-methylaminobenzylcyanide (3.05 g, 20.9 mmol), epichlorohydrine (2.4 ml, 2.87 g, 31 mmol), ethanol (25 ml) and water (20 ml) was heated under reflux for 3 hours. After cooling the mixture was diluted with ethanol (10 ml) followed by addition of aqueous 10N NaOH (6 ml). The obtained clear solution was stirred at room temperature for one hour and the ethanol was distilled off. The residue was diluted with 100 ml of water and extracted with ether (3×50 ml). The organic extracts were washed with brine until neutral, dried over MgSO4 and concentrated. The residue was chromatographed over a silica gel column eluting with a 3:1 mixture of benzene and ethyl acetate to give 2.21 g of the oily title compound, yield: 52.2%.

1. temperaturewas heated
2. temperatureunder reflux for 3 hours
3. temperatureAfter cooling the mixture
4. distillationthe ethanol was distilled off
5. additionThe residue was diluted with 100 ml of water
6. extractionextracted with ether (3×50 ml)
7. washThe organic extracts were washed with brine until neutral,
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe residue was chromatographed over a silica gel column
11. washeluting with a 3:1 mixture of benzene and ethyl acetate

ORD record

ord-c3d67726ec814bf09157e6f4c0b9c9bb

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380724