Formaldehyde → 3-(Dimethylamino)-1-(5-methoxy-1-methyl-1H-indol-3-yl)-1-propanone hydrochloride hemihydrate

HRID 1194349Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1194349
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13](=[O:15])[CH3:14].[CH2:16]=O.[ClH:18].[CH3:19][NH:20][CH3:21]>C(O)C>[OH2:2].[ClH:18].[CH3:19][N:20]([CH3:16])[CH2:21][CH2:14][C:13]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:8]([CH3:12])[CH:7]=1)=[O:15].[CH3:19][N:20]([CH2:16][CH2:14][C:13]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:8]([CH3:12])[CH:7]=1)=[O:15])[CH3:21].[ClH:18]

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 212700281-(5-Methoxy-1-methyl-1H-indol-3-yl)ethan-1-one

Produkt 1

HCID 700459593-(Dimethylamino)-1-(5-methoxy-1-methyl-1H-indol-3-yl)-1-propanone hydrochloride hemihydrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(5-methoxy-1-methyl-1H-indol-3-yl)-1-ethanone (0.23 g), paraformaldehyde (0.07 g) and dimethylamine hydrochloride (0.2 g) in ethanol (20 ml) was heated at reflux for 24 h, cooled, and the solvent was evaporated in vacuo. The residue was partitioned between sodium carbonate (2N; 50 ml) and ethyl acetate (2×50 ml). The combined organic extracts were dried and evaporated in vacuo to give an oil, which was purified by FCC eluting with System A to give the free base of the title compound as an oil. This was dissolved in absolute ethanol (5 ml) acidified with ethanolic hydrogen chloride, and the salt was precipitated by the addition of excess dry ether (100 ml). The salt was filtered off and dried in vacuo to give the title compound (0.1 g), m.p. 210°-211°.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was partitioned between sodium carbonate (2N; 50 ml) and ethyl acetate (2×50 ml)
  6. customThe combined organic extracts were dried
  7. customevaporated in vacuo
  8. customto give an oil, which
  9. customwas purified by FCC
  10. washeluting with System A

Quellen und Nachweise

ORD-Eintrag
ord-9b9d20f39774446f835bc8e0b6fc8660
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04814344

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