Potassium Iodide → alpha-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(5-methoxyl-[1H]-indol-3-yl)-1-piperidine-ethanol

HRID 866653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866653
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.Cl[CH2:19][CH:20]([C:22]1[O:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[O:24][CH:23]=1)[OH:21].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[O:27]1[C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[O:24][CH2:23][CH:22]1[CH:20]([OH:21])[CH2:19][N:15]1[CH2:16][CH2:17][CH:12]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:8][CH:7]=2)[CH2:13][CH2:14]1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 432245-Methoxy-3-(piperidin-4-yl)-1H-indoleHCID 12733300alpha-(Chloromethyl)-1,4-benzodioxin-2-methanol

Produkt 1

HCID 20320076alpha-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(5-methoxyl-[1H]-indol-3-yl)-1-piperidine-ethanolAusbeute 111,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4.6 g of 4-(5-methoxy-[1H]-indol-3-yl)-piperidine, 4.3 g of α-(chloromethyl)-1,4-benzodioxin-2-methanol, 4.4 g of sodium carbonate, 3.3 g of potassium iodide and 25 ml of dimethylformamide was heated with stirring at 100° C for 24 hours under a nitrogen atmosphere and then the mixture was cooled and filtered. The filter was washed with dimethylformamide and the filtrate was evaported under reduced pressure to dryness. The residue was taken up in a 1--1 mixture of water and methylene chloride and the organic phase was recovered by decantation, was washed, dried and evaporated to dryness under reduced pressure to obtain 9.1 g of α-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(5-methoxyl-[1H]-indol-3-yl)-1-piperidine-ethanol in the form of a mixture of 2 diastereoisomeric racemates in the form of a brown oil which was used as is for the next step.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. washThe filter was washed with dimethylformamide
  5. additionThe residue was taken up in a 1--1 mixture of water and methylene chloride
  6. customthe organic phase was recovered by decantation
  7. washwas washed
  8. customdried
  9. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b77795fa04224a02b7fb77b39efcdcc0
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04100291

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