Hydrochloric Acid → 3-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one

HRID 1085626

Reaktionsgleichung

Cl.[CH3:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1)=[O:4].Cl.[CH3:18][NH:19][CH3:20].[CH2:21]=O>C(O)C.CC(C)=O>[CH3:18][N:19]([CH2:21][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1)=[O:4])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Concentrated hydrochloric acid (1 mL) was added to a stirred mixture of 3,4,5-trimethoxyacetophenone (210 g, 1 mole), dimethylamine hydrochloride (81 g, 1 mole) and paraformaldehyde (45 g, 1.5 mole) in ethanol (300 mL). The reaction mixture was heated under reflux for 1 hour. Another portion of paraformaldehyde (30 g, 1 mole) was added, and the heating was continued for another 2 hours. The warm reaction mixture was poured with vigorous stirring into acetone (2.4 L). The slurry was heated at 60° C. for 15 minutes, cooled, and filtered. The solid was washed with acetone and dried to provide the hydrochloride salt of 3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one, R, 0.05 (SiO2, 2:1 [v/v] hexane-ethyl acetate); m.p. 175° C. A mixture of the above hydrochloride (147.5 g, 0.48 mole) in 1 N NaOH (750 mL) was shaken with ethyl acetate (4×100 mL). The combined organic extracts were washed with brine, dried, and evaporated in vacuo to provide 3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one.

Aufarbeitung

temperatureThe reaction mixture was heated
temperatureunder reflux for 1 hour
customThe warm reaction mixture
additionwas poured
temperaturecooled
filtrationfiltered
washThe solid was washed with acetone
customdried

Quellen und Nachweise

ORD-Eintrag: ord-e1b069017dad44c49678d1695b56f89a
Quelldatensatz: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05010100

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