3-Chloro-4-(trifluoromethyl)aniline → HCID 11596912, Verbindung

HRID 603164

Reaktionsgleichung

Reaktionsgleichung von HRID 603164
[C:1](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:2].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([Cl:27])[CH:18]=1.[CH3:28][N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([CH2:35][N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:30]1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:27][C:19]1[CH:18]=[C:17]([NH:16][C:1]([N:39]2[CH2:40][CH2:41][N:36]([CH2:35][CH:31]3[CH2:32][CH2:33][CH2:34][N:29]([CH3:28])[CH2:30]3)[CH2:37][CH2:38]2)=[O:2])[CH:22]=[CH:21][C:20]=1[C:23]([F:24])([F:25])[F:26]

Komponenten

6

Edukt 3

HCID 679623-Chloro-4-(trifluoromethyl)anilineHCID 90495Di-tert-butyl dicarbonateHCID 27369401-[(1-Methylpiperidin-3-yl)methyl]piperazine

Produkt 1

HCID 11596912HCID 11596912, VerbindungAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

To a solution of di-tert-butyl dicarbonate (114.6 mg) in chloroform (2 ml) was added 4-dimethylaminopyridine (6 mg). A solution of 4-amino-2-chlorobenzotrifluoride (98.1 mg) in chloroform (2 ml) was added and the reaction mixture stirred for 20 minutes at room temperature. A solution of 1-[(1-methylpiperidin-3-yl)methyl]piperazine (98.5 mg) in chloroform (2 ml) was added and the resulting solution was stirred at reflux for 18 hours. The reaction mixture was purified by column chromatography on silica gel (20 g) using a gradient of 100% dichloromethane through to 20% methanolic ammonia in dichloromethane to give the title compound (14 mg).

Aufarbeitung

  1. stirringthe resulting solution was stirred
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was purified by column chromatography on silica gel (20 g)

Quellen und Nachweise

ORD-Eintrag
ord-756c6bebf35b4f39a1dcfd943e37587b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906645B2

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