Water → 4-[(4,5-Difluoro-2-methoxyphenoxy)methyl]-N-(triphenylmethyl)-1-piperidineethanamine

HRID 248347

Reaktionsgleichung

Reaktionsgleichung von HRID 248347
Cl.[F:2][C:3]1[C:16]([F:17])=[CH:15][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[C:5]([O:18][CH3:19])[CH:4]=1.Br[CH2:21][CH2:22][NH:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:2][C:3]1[C:16]([F:17])=[CH:15][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:21][CH2:22][NH:23][C:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:11][CH2:10]2)=[C:5]([O:18][CH3:19])[CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15718287(2-Bromoethyl)tritylamineHCID 19763367HCID 19763367, Verbindung

Produkt 1

HCID 197633854-[(4,5-Difluoro-2-methoxyphenoxy)methyl]-N-(triphenylmethyl)-1-piperidineethanamineAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5.88 g (0.020 mol) of 4-[(4,5-difluoro-2-methoxyphenoxy)methyl]piperidine hydrochloride, 7.7 g (0.021 mol) of 2-bromo-N-(triphenylmethyl)ethylamine and 6.91 g (0.050 mol) of K2CO3 in 40 ml of DMF are reacted. The reaction mixture is heated to 90° C. for 8 hours. It is cooled to room temperature, poured into 500 ml of water and extracted 3 times with ethyl acetate. The organic phases are combined, washed with water, dried over MgSO4 and filtered, and the solvent is evaporated off under reduced pressure. The product is obtained in the form of an oil after chromatography. Yield: 41.5%.

Aufarbeitung

  1. temperatureIt is cooled to room temperature
  2. extractionextracted 3 times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe product is obtained in the form of an oil after chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d32e64f01da745f7a4d7dbc8a579c938
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05210086

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