Methanol → 2-Trifluoromethyl-10-[3-(3-caproyloxypyrrolidino)-propyl]-phenothiazine

HRID 1981292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1981292
Cl.[F:2][C:3]([F:28])([F:27])[C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]3)[C:6]=2[CH:5]=1.[C:29](Cl)(=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].CO>ClC(Cl)C>[F:28][C:3]([F:27])([F:2])[C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH:23]([O:26][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22]3)[C:6]=2[CH:5]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 67340Hexanoyl chlorideHCID 16298210-(3-(3-Hydroxypyrrolidinyl)propyl)-2-trifluoromethylphenothiazine

Produkt 1

HCID 127695112-Trifluoromethyl-10-[3-(3-caproyloxypyrrolidino)-propyl]-phenothiazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

8.6 G. of 2-trifluoromethyl-10-[3-(3-hydroxypyrrolidino)-propyl]-phenothiazine.hydrochloride were dissolved in 100 ml of dichloroethane. To the solution were added drop by drop 3.0 g of caproylchloride at a room temperature with stirring. This mixture was heated under reflux for two hours. After cooling, 20 ml of methanol were added to said mixture, and the whole was stirred for about 1 hour. The resulting reaction mixture was washed, in turn, with water, aqueous potasium carbonate solution and water respectively, and dried over sodium sulphate. The solvent was distilled off under a reduced pressure. The resulting pale brown oily material was purified by means of silicagel column chromatography (solvent for elution: the mixed solvent of n-hexan.ethylacetate), thereby obtaining the object as the free base, which was pale yellowish viscous liquid.

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureunder reflux for two hours
  3. temperatureAfter cooling
  4. stirringthe whole was stirred for about 1 hour
  5. customThe resulting reaction mixture
  6. washwas washed, in turn, with water, aqueous potasium carbonate solution and water respectively
  7. dry with materialdried over sodium sulphate
  8. distillationThe solvent was distilled off under a reduced pressure
  9. customThe resulting pale brown oily material was purified by means of silicagel column chromatography (solvent
  10. washfor elution
  11. customethylacetate), thereby obtaining the object as the free base, which

Quellen und Nachweise

ORD-Eintrag
ord-233bfc09f3b7426d8f320c01858c1cd0
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04514395

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