Sodium Iodide → 2-Butanol, 3-((1-(3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-4-piperidinyl)oxy)-

HRID 329038

Reaktionsgleichung

Reaktionsgleichung von HRID 329038
[I-].[Na+].Cl[CH2:4][CH2:5][CH2:6][N:7]1[C:20]2[CH:19]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.C(N(CC)CC)C.[CH3:32][CH:33]([OH:43])[CH:34]([CH3:42])[O:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>C(C(C)=O)C>[F:22][C:21]([F:24])([F:23])[C:18]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]([CH2:6][CH2:5][CH2:4][N:39]3[CH2:40][CH2:41][CH:36]([O:35][CH:34]([CH3:42])[CH:33]([CH3:32])[OH:43])[CH2:37][CH2:38]3)[C:20]=2[CH:19]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazineHCID 214409071,2-Dimethyl-2-(4-piperidyloxy)-ethanol

Produkt 1

HCID 2180932-Butanol, 3-((1-(3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-4-piperidinyl)oxy)-Ausbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

22.5 g (0.15 mole) of sodium iodide were added to a solution of 51.5 g (0.15 mole) of 10-(3-chloropropyl)-2-trifluoromethyl-phenothiazine in 400 ml of methyl ethyl ketone followed by the addition of 15.2 g (0.15 mole) of triethylamine and then 26 g (0.15 mole) of 1,2-dimethyl-2-(4-piperidyloxy)-ethanol. The mixture was then refluxed for 20 hours and after cooling, the precipitate formed was removed by vacuum filtration. The filtrate was evaporated to dryness and the oil residue was chromatographed over 1 kg of neutral alumina. Elution with ethyl acetate gave 34.5 g (48% yield) of 2-trifluoromethyl-10-[3-(4-[1,2-dimethyl-2-hydroxyethoxy]-piperidino)-propyl]-phenothiazine in the form of a clear amber oil.

Aufarbeitung

  1. temperatureThe mixture was then refluxed for 20 hours
  2. temperatureafter cooling
  3. customthe precipitate formed
  4. customwas removed by vacuum filtration
  5. customThe filtrate was evaporated to dryness
  6. customthe oil residue was chromatographed over 1 kg of neutral alumina
  7. washElution with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e8008bdff8df4e0796e205ef0c9844a3
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018922

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