Hydrochloric Acid → HCID 178505486, Verbindung

HRID 561210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561210
[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]#[N:17])[O:13][N:12]=2)[CH2:7][CH2:6]1.Cl.[NH+]1C=CC=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+].Cl>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]3[NH:32][N:31]=[N:30][N:17]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 21584435Pyridinium hydrochlorideHCID 533885303-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carbonitrile

Produkt 1

HCID 178505486HCID 178505486, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carbonitrile (1.4 g, 3.82 mmol), pyridinium hydrochloride (0.9 g, 7.79 mmol) and sodium azide (1.3 g, 20.00 mmol) in NMP (12 mL) was stirred and heated at 130° C. bath for 2 h. After cooling, the mixture was diluted with water and acidified with 1N HCl (some precipitate appeared). The whole mixture was then extracted with EtOAc. The EtOAc extract was washed with water (3×), dried (Na2SO4) and concentrated. The residue was triturated with diethyl ether to give the title compound as a light brown powder.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe whole mixture was then extracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with water (3×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7bbc3825a6b04ff7bbd2aa8177bc8d01
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063224B2

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