Sodium Iodide → {4-[1-(4-Chloro-phenyl)-cyclohexyl]-thiazol-2-yl}-(3-morpholin-4-yl-propyl)-amine

HRID 47277

Reaktionsgleichung

Reaktionsgleichung von HRID 47277
Cl[CH2:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[I-].[Na+].[O:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][NH:29][C:30]([NH2:32])=[S:31])[CH2:22][CH2:21]1>CC(C)=O.C(=O)([O-])O.[Na+].O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:5]2([C:3]3[N:32]=[C:30]([NH:29][CH2:28][CH2:27][CH2:26][N:23]4[CH2:22][CH2:21][O:20][CH2:25][CH2:24]4)[S:31][CH:2]=3)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:12][CH:13]=1

Komponenten

7

Edukt 3

HCID 5238Sodium IodideHCID 2760135N-[3-(4-Morpholinyl)propyl]thioureaHCID 219923432-Chloro-1-[1-(4-chloro-phenyl)-cyclohexyl]-ethanone

Produkt 1

HCID 21992318{4-[1-(4-Chloro-phenyl)-cyclohexyl]-thiazol-2-yl}-(3-morpholin-4-yl-propyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 2-chloro-1-[1-(4-chloro-phenyl)-cyclohexyl]-ethanone (191.5 mg, 0.71 mmol) and sodium iodide (105.8 mg, 0.71 mmol) in acetone (5 mL) was stirred at room temperature for 10 min. Next, 1-(3-morpholinopropyl)-2-thiourea (143.6 mg, 0.71 mmol) was added. The resulting mixture was heated at 50° C. overnight. After the mixture was allowed to cool to room temperature, it was diluted with 5% sodium hydrogen carbonate in water and then extracted with ethyl acetate (3×20 mL). The extracts were combined, and dried over anhydrous sodium sulfate, filtered and concentrated to give an oil. The crude was purified by column chromatography on silica gel using dichloromethane/2 N ammonia in ethanol (95:5) to give {4-[1-(4-chloro-phenyl)-cyclohexyl]-thiazol-2-yl}-(3-morpholin-4-yl-propyl)-amine, 94, as an oil (187.1 mg, 63%). 1H (CDCl3, 300 MHz) δ 7.31-7.21 (m, 4H), 6.01 (s, 1H), 5.93 (s, 1H), 3.70-1.52 (m, 24H) ppm;13C (C6D6, 75 MHz) δ 23.5, 25.5, 26.9, 36.7, 45.7, 46.4, 54.2, 57.7, 67.4, 101.3, 128.8, 129.4, 132.0, 146.8, 160.1, 169.5 ppm.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a8e36bf78fc84311a1696c8d9b0a7bc2
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699866B2

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