Triethylamine → 2-Trifluoromethyl-10-[3-(4-heptyl-4-beta-hydroxy-ethoxy-piperidino)-beta-propyl]-phenothiazine hydrochloride

HRID 329049

Reaktionsgleichung

Reaktionsgleichung von HRID 329049
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:17][CH2:18]C[Cl:20])[C:5]=2[CH:4]=1.[CH2:23](N(CC)CC)C.[CH2:30]([C:37]1([O:43][CH2:44][CH2:45][OH:46])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(C(C)=O)C.[I-].[Na+]>[ClH:20].[F:21][C:2]([F:22])([F:1])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH:17]([CH2:23][N:40]3[CH2:41][CH2:42][C:37]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([O:43][CH2:44][CH2:45][OH:46])[CH2:38][CH2:39]3)[CH3:18])[C:5]=2[CH:4]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazineHCID 214409012-(4-Heptyl-4-piperidyloxy)-ethanol

Produkt 1

HCID 706346132-Trifluoromethyl-10-[3-(4-heptyl-4-beta-hydroxy-ethoxy-piperidino)-beta-propyl]-phenothiazine hydrochlorideAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel2×

Versuchsvorschrift

14.1 g of 2-trifluoromethyl-10-(3-chloropropyl)-phenothiazine were dissolved in 50 ml of methyl ethyl ketone and 6.14 g of sodium iodide, 4.15 g of triethylamine, then 10 g of 2-(4-heptyl-4-piperidyloxy)-ethanol dissolved in 50 ml of methyl ethyl ketone were successively added thereto. The mixture was refluxed with agitation for 40 hours and after cooling, the precipitate formed was removed by vacuum filtration. The organic solution was washed with an aqueous solution of sodium bicarbonate, then with water, dried and then concentrated. The said product was reacted with an ether solution of hydrogen chloride and the obtained precipitate was recovered by vacuum filtration and was crystallized from an ethanol ether mixture to obtain 7.8 g of 2-trifluoromethyl-10-[3-(4-heptyl-4-β-hydroxy-ethoxy-piperidino)-β-propyl]-phenothiazine hydrochloride as white crystals melting at 180° C and soluble in ethanol and insoluble in water and ether.

Aufarbeitung

  1. additionwere successively added
  2. temperatureThe mixture was refluxed with agitation for 40 hours
  3. temperatureafter cooling
  4. customthe precipitate formed
  5. customwas removed by vacuum filtration
  6. washThe organic solution was washed with an aqueous solution of sodium bicarbonate
  7. dry with materialwith water, dried
  8. concentrationconcentrated
  9. customThe said product was reacted with an ether solution of hydrogen chloride
  10. filtrationthe obtained precipitate was recovered by vacuum filtration
  11. customwas crystallized from an ethanol ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-2ac11dbfba764ba3a22b4f086f28994b
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018922

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