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

HRID 265627

Reaktionsgleichung

Reaktionsgleichung von HRID 265627
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].[CH2:16]=O.Cl.[CH3:19][NH:20][CH3:21].Cl>C(O)C.O>[CH3:19][N:20]([CH2:16][CH2:1][C:2]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:12][CH3:13])=[C:8]([O:10][CH3:11])[CH:9]=1)=[O:3])[CH3:21]

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 712Formaldehyde2×HCID 10473Dimethylamine, hydrochloride2×HCID 143453',4',5'-Trimethoxyacetophenone

Produkt 1

HCID 4123063-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3,4,5-Trimethoxyacetophenone (50 g, 237.8 mmole), paraformaldehyde (9.75 g, 304.7 mmole), dimethylamine hydrochloride (26.42 g, 324.0 mmole) and 5 mL conc. HCl were dissolved in 200 mL absolute ethanol and refluxed for 10 hours. Additional dimethylamine hydrochloride (13.21 g, 162.0 mmole) and paraformaldehyde (9.75 g, 304.7 mmole) were added and the solution returned to reflux. Alter 54 hours (total reaction time), 80 mL of 10% HCl and 500 mL of water were added and the solution was extracted with ethyl ether. The acidic aqueous layer was adjusted to pH 10 with 10% NaOH. The basic solution was extracted with ethyl acetate, dried over MgSO4, filtered and evaporated in vacuo to provide 57.5 g of a yellow oil (92%). 1H NMR (CDCl3): 2.30 (s, 6H); 2,74 (t, 2H); 3.11 (t, 3H); 3.91 (s, 9H); 7.23 (s, 1H); 7.32 (s, 1H).

Aufarbeitung

  1. temperaturerefluxed for 10 hours
  2. temperatureto reflux
  3. extractionthe solution was extracted with ethyl ether
  4. extractionThe basic solution was extracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-372ed01939a246048f316b93e524779d
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648486

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