Ammonium Chloride → HCID 178506150, Verbindung

HRID 419701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419701
O=[C:2]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]1)=O.[NH4+:30].[Cl-]>C(O)C>[F:27][C:26]([F:29])([F:28])[C:22]1[CH:21]=[C:20]([C:2]2[N:30]=[C:5]([CH:7]3[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]3)[NH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 25517Ammonium Chloride3×HCID 57751897Tert-butyl 4-((2-oxo-2-(3-(trifluoromethyl)phenyl)ethyl)carbamoyl)piperidine-1-carboxylate3×

Produkt 1

HCID 178506150HCID 178506150, VerbindungAusbeute 189,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel3×

Versuchsvorschrift

Microwave heat a mixture of tert-butyl 4-(2-oxo-2-(3-(trifluoromethyl)phenyl)-ethylcarbamoyl)piperidine-1-carboxylate (2.5 g, 6.09 mmol) and NH4Cl (1.68 g, 31.4 mmol) in ethanol (20 mL) at 300 W, 120° C., and 200 PSI for 16 h in a CEM Discover microwave apparatus. Cool the mixture to room temperature. Repeat the procedure with a second portion of tert-butyl 4-(2-oxo-2-(3-(trifluoromethyl)phenyl)ethylcarbamoyl)-piperidine-1-carboxylate (2.35 g, 5.67 mmol) and NH4Cl (1.8 g, 33.6 mmol) in ethanol (20 mL) utilizing the same microwave and heating program. Cool the mixture to room temperature. Repeat the above procedure with a third portion of tert-butyl 4-(2-oxo-2-(3-(trifluoromethyl)phenyl)ethylcarbamoyl)piperidine-1-carboxylate (2.0 g, 4.82 mmol) and NH4Cl (1.34 mg, 25.0 mmol) in ethanol (15 mL) at 300 W, 160° C., and 200 PSI for 12 h in a microwave apparatus. Cool the mixture to room temperature. Combine the batches, adsorb onto silica gel, and concentrate in vacuo. Purify the residue by silica gel chromatography (120 g RediSep column, eluting with a gradient of 0% through 100% CMA:methylene chloride, 3 L) to provide 4-(4-(3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidine (3.40 g, 75%).

Aufarbeitung

  1. temperatureMicrowave heat
  2. temperatureheating program
  3. temperatureCool the mixture to room temperature
  4. temperatureCool the mixture to room temperature
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by silica gel chromatography (120 g RediSep column
  7. washeluting with a gradient of 0% through 100% CMA

Quellen und Nachweise

ORD-Eintrag
ord-0043f39608c9427698889da3928f7c27
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093383B2

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