Methylamine → HCID 22791903, compound

To a 13.4% solution of methylamine in 100 ml of abs. ethanol was added 5.0 g (10.7 mmol) of 3-(3-phthalimidopropoxy)-7,8-didehydro-4,5α-epoxy-17-methylmorphinan-6 α-ol. After stirring at room temperature for 3.5 hrs, the reaction mixture was concentrated to a volume of about 50 ml and diluted with 200 ml of water and 200 ml of chloroform. The organic solution was separated and the aqueous phase was extracted with chloroform (2 × 200 ml). The combined chloroform solution was extracted with 1 N hydrochloric acid (2 × 100 ml). The acidic extracts were combined and made basic with 2 N sodium hydroxide (150 ml). The aqueous suspension was extracted with chloroform (3 × 200 ml). The chloroform solution was washed with water (2 × 200 ml) and dried. Removal of solvent in vacuo afforded 3.8 g of crude product, which, after recrystallization from benzene-ether, yielded pure 3-(3-aminopropoxy)-7,8-didehydro-4,5α-epoxy-17-methylmorphinan-6α-ol, m.p. 132°-134°[α]D25 -110.2°(c 1.06, MeOH).

1. concentrationthe reaction mixture was concentrated to a volume of about 50 ml
2. additiondiluted with 200 ml of water and 200 ml of chloroform
3. customThe organic solution was separated
4. extractionthe aqueous phase was extracted with chloroform (2 × 200 ml)
5. extractionThe combined chloroform solution was extracted with 1 N hydrochloric acid (2 × 100 ml)
6. extractionThe aqueous suspension was extracted with chloroform (3 × 200 ml)
7. washThe chloroform solution was washed with water (2 × 200 ml)
8. customdried
9. customRemoval of solvent in vacuo
10. customafforded 3.8 g of crude product, which
11. customafter recrystallization from benzene-ether

ORD record

ord-731a5401cb334251afdf95864958e644

Source dataset

uspto-grants-1976_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03972992