Potassium Carbonate → N-(3,3-diphenylpropyl)pyridin-3-amine

HRID 2190306

Reaktionsgleichung

Reaktionsgleichung von HRID 2190306
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]1([CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16][NH2:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CCOC(C)=O.[Cu]I.CS(C)=O>[C:18]1([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:15][CH2:16][NH:17][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 707143-IodopyridineHCID 796983,3-DiphenylpropylamineHCID 145742L-Proline

Produkt 1

HCID 3059709N-(3,3-diphenylpropyl)pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a mixture of 3-iodopyridine (1.12 g, 5.46 mmol) and 3,3-diphenylpropan-1-amine (1.72 g, 8.14 mmol) was added potassium carbonate (1.49 g, 10.8 mmol), copper(I) iodide (0.126 g, 0.662 mmol), (S)-pyrrolidine-2-carboxylic acid (0.154 g, 1.34 mmol), and DMSO (3.5 mL). The reaction mixture was heated to 75° C. for 18 h and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 30% to 80% EtOAc in hexanes) gave N-(3,3-diphenylpropyl)pyridin-3-amine.

Aufarbeitung

  1. washThe organic phase was washed with water (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (eluted with 30% to 80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2734f1daeeaa4b488d6e77090b0ea605
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324396B2

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