Potassium Hydroxide → HCID 11276773, Verbindung

HRID 1059695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059695
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17]C(=O)C(F)(F)F)[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 18630938HCID 18630938, Verbindung

Produkt 1

HCID 11276773HCID 11276773, VerbindungAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-{3-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-2,2,2-trifluoroacetamide (1.77 g, 5.10 mmol) and 20% aqueous KOH (25 mL) in ethanol (50 mL) were stirred at room temperature for 30 minutes. The reaction mixture was concentrated to dryness and the solids were washed with methylene chloride, dried over magnesium sulfate and concentrated to give 3-[4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-propylamine (0.82 g, 64%) as a waxy white solid. Mp. 57-58° C.; NMR CDCl3 δ 7.29-7.20 (m, 4H), 6.03 (s, 1H), 3.12 (d, J=3.3 Hz, 2H), 2.76 (t, J=6.9 Hz, 2H), 2.67 (t, J=5.6 Hz, 2H), 2.51-2.44 (m, 4H), 1.69 (p, J=7.5 Hz, 2H), 1.63 (s, 2H); 13C NMR CDCl3 δ 139.20, 133.96, 132.61, 128.36, 126.15, 122.41, 56.20, 53.36, 50.30, 40.77, 30.73, 28.01; IR(KBr) 2929, 2861, 2805, 2767, 2734, 1493, 1467, 1379, 1320, 1128, 1095, 845, 825, 800; Analysis calculated for C14H19CIN2.0.25H2O: C, 65.87; H, 7.70; N, 10.97. Found: C, 65.69; H, 7.44; N, 10.91.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washthe solids were washed with methylene chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4d1c9290411140e094453b77383fb627
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521630B1

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