Triethylamine → 2-Trifluoromethyl-10-[3-(4-beta-hydroxyethoxy-4-ethyl-piperidino)-propyl]-phenothiazine hydrochloride

HRID 329047

Reaktionsgleichung

Reaktionsgleichung von HRID 329047
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:18]2[CH:17]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:14][C:13]=2[S:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.C(N(CC)CC)C.[CH2:30]([C:32]1([O:38][CH2:39][CH2:40][OH:41])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH3:31]>C(C(C)=O)C.[I-].[Na+]>[ClH:1].[F:20][C:19]([F:22])([F:21])[C:16]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:4][CH2:3][CH2:2][N:35]3[CH2:36][CH2:37][C:32]([O:38][CH2:39][CH2:40][OH:41])([CH2:30][CH3:31])[CH2:33][CH2:34]3)[C:18]=2[CH:17]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazineHCID 214409042-(4-Ethyl-4-piperidyloxy)-ethanol

Produkt 1

HCID 706347182-Trifluoromethyl-10-[3-(4-beta-hydroxyethoxy-4-ethyl-piperidino)-propyl]-phenothiazine hydrochlorideAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel2×

Versuchsvorschrift

37.7 g of 10-(3-chloropropyl)-2-trifluoromethyl-phenothiazine were dissolved in 100 ml of methyl ethyl ketone and 16.5 g of sodium iodide, 11.1 g of triethylamine and then 19 g of 2-(4-ethyl-4-piperidyloxy)-ethanol dissolved in 100 ml of methyl ethyl ketone were successively added thereto. The mixture was refluxed for 20 hours and after cooling, the precipitate formed was removed by vacuum filtration. The filtrate was evaporated to dryness and the residue was dissolved in methylene chloride. The organic solution was washed with an aqueous solution of sodium bicarbonate, then with water, dried and concentrated to dryness. The residue was dissolved in an ethanol-ether mixture to which was added an ether solution of hydrogen chloride. The precipitate formed was recovered by vacuum filtration and was crystallized from isopropanol, then from acetonitrile to obtain 27 g of 2-trifluoromethyl-10-[3-(4-β-hydroxyethoxy-4-ethyl-piperidino)-propyl]-phenothiazine hydrochloride as white crystals, melting at 204° C and soluble in chloroform, water, dilute hydrochloride acid and methylene chloride.

Aufarbeitung

  1. additionwere successively added
  2. temperatureThe mixture was refluxed for 20 hours
  3. temperatureafter cooling
  4. customthe precipitate formed
  5. customwas removed by vacuum filtration
  6. customThe filtrate was evaporated to dryness
  7. dissolutionthe residue was dissolved in methylene chloride
  8. washThe organic solution was washed with an aqueous solution of sodium bicarbonate
  9. dry with materialwith water, dried
  10. concentrationconcentrated to dryness
  11. dissolutionThe residue was dissolved in an ethanol-ether mixture to which
  12. additionwas added an ether solution of hydrogen chloride
  13. customThe precipitate formed
  14. filtrationwas recovered by vacuum filtration
  15. customwas crystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-05916d27420145eebeb59d07122a90c9
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018922

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