Diethylamine → HCID 12828476, compound

A mixture of 5.0 g of 1-chloromethyl-6-methoxyisochroman and 30 ml of diethylamine was heated in a sealed tube at 150°-160° C for 21 hours and, after cooling, the reaction mixture was concentrated under reduced pressure. The residue was diluted with 100 ml of water and extracted with chloroform. The extract was rinsed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel, and elution was carried out with a 1:2 mixture of benzene and methanol. The oily product thus obtained was converted to the fumarate and recrystallized from a mixture of methanol and ether. By the above procedure was obtained 1.9 g of 1-diethylaminomethyl-6-methoxyisochroman fumarate as colorless prisms.

1. temperaturewas heated in a sealed tube at 150°-160° C for 21 hours
2. temperatureafter cooling
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. additionThe residue was diluted with 100 ml of water
5. extractionextracted with chloroform
6. washThe extract was rinsed with water
7. customdried
8. concentrationconcentrated under reduced pressure
9. customThe residue was chromatographed on a column of silica gel, and elution
10. additionwas carried out with a 1:2 mixture of benzene and methanol
11. customThe oily product thus obtained
12. customrecrystallized from a mixture of methanol and ether

ORD record

ord-19fb5a2ff62e49f49b3b0cda84364f3f

Source dataset

uspto-grants-1978_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04066648