Potassium Carbonate → N-[2,4-bis(trifluoromethyl)benzyl]-N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine

HRID 2251520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251520
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[F:24][C:25]([F:39])([F:38])[C:26]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:27]=1[CH2:28]Br>O1CCOCC1>[F:24][C:25]([F:38])([F:39])[C:26]1[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=[CH:30][C:27]=1[CH2:28][N:11]([CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 28549389N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine

Produkt 1

HCID 86598930N-[2,4-bis(trifluoromethyl)benzyl]-N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine (150 mg; 0.66 mmol) in 3 ml of dioxane, under nitrogen, was treated with K2CO3 (113 mg; 0.82 mmol) and 2,4-bis-trifluoromethyl-benzyl bromide (0.13 ml; 0.69 mmol) and heated in a pressure tube at 190–220C for 16 hours. Upon cooling, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with saturated brine, dried over sodium sulfate and concentrated. Purification by radial chromatography on silica gel using an ethyl acetate-hexane gradient (5–50%) afforded N-[2,4-bis(trifluoromethyl)benzyl]-N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine (130 mg; 44% yield).

Aufarbeitung

  1. temperatureheated in a pressure tube at 190–220C for 16 hours
  2. temperatureUpon cooling
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by radial chromatography on silica gel using an ethyl acetate-hexane gradient (5–50%)

Quellen und Nachweise

ORD-Eintrag
ord-507e680acfc14de5baa0c243d38db227
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319104B2

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