Formaldehyde → 1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(dimethylamino)propan-1-one

HRID 1410274

Reaktionsgleichung

Reaktionsgleichung von HRID 1410274
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11](=[O:13])[CH3:12])[CH:9]=[CH:10][C:2]1=2.Cl.[CH3:15][NH:16][CH3:17].[CH2:18]=O>Cl.C(O)C>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11](=[O:13])[CH2:12][CH2:15][N:16]([CH3:18])[CH3:17])[CH:9]=[CH:10][C:2]1=2

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 761431,4-Benzodioxan-6-yl methyl ketone

Produkt 1

HCID 28250181-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-(dimethylamino)propan-1-oneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanone (XV) (11 mmol), dimethylamine hydrochloride (14 mmol), paraformaldehyde (16 mmol) and 12 N HCl (2 drops) in ethanol (5 mL) was refluxed overnight. The solution was cooled to room temperature and the ethanol was evaporated under vacuum. The residue was treated with ethyl acetate, heated slightly and sonicated to disperse into fine particles. The solids were filtered and dried at room temperature to produce 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino)propan-1-one (XVI) as a white solid, (82% yield), 1H NMR (CDCl3, 400 MHz): δ ppm 2.77 (s, 6H), 3.41 (m, 2H), 3.56 (m, 2H), 4.25 (m, 4H), 6.85 (m, 1H), 7.45 (m, 2H).

Aufarbeitung

  1. customthe ethanol was evaporated under vacuum
  2. additionThe residue was treated with ethyl acetate
  3. temperatureheated slightly
  4. customsonicated
  5. additionto disperse into fine particles
  6. filtrationThe solids were filtered
  7. customdried at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-a49a61ad0a894e098379c8482865edc3
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921413B2

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