4-methoxy-N-ethylamphetamine → 1-(2-{Ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-one

A mixture of [2-(4-methoxyphenyl)-1-methylethyl]ethylamine (0.53 g, 2.75 mmole), (2-oxo-azepan-1-yl)acetaldehyde (0.5 g, 3.2 mmole), and sodium triacetoxyborohydride (0.88 g, 4.1 mmole) in 1,2-dichloroethane (15 mL) was stirred at room temperature for 60 hours. The mixture was concentrated, and the residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL). The organic solution was extracted with 5% hydrochloric acid (20 mL), and the aqueous acidic phase was washed with diethyl ether and the pH was adjusted to 12 with 25% sodium hydroxide. The mixture was extracted with dichoromethane, and the organic phase was dried (sodium sulfate) and concentrated to give 1-(2-{ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-one 11(0.84 g) as a viscous oil, which was converted to the dibenzoyl-L-tartrate salt, Anal.: Calcd. for C38H46N2O10: C, 66.07; H, 6.71; N, 4.06%; Found C, 64.69; H, 6.45; N 3.90%.

1. concentrationThe mixture was concentrated
2. customthe residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
3. extractionThe organic solution was extracted with 5% hydrochloric acid (20 mL)
4. washthe aqueous acidic phase was washed with diethyl ether
5. extractionThe mixture was extracted with dichoromethane
6. dry with materialthe organic phase was dried (sodium sulfate)
7. concentrationconcentrated

ORD-Eintrag

ord-0cc6d0e7211f4b558fcc0dfdeecc9391

Quelldatensatz

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06667301B2