Hydrochloric Acid → 2,6-Difluoro-4-morpholin-4-yl-phenylamine

HRID 905575

Reaktionsgleichung

Reaktionsgleichung von HRID 905575
Cl.[F:2][C:3]1[CH:4]=[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[C:7]([F:12])[C:8]=1[N+:9]([O-])=O>O1CCCC1.[Zn]>[F:12][C:7]1[CH:6]=[C:5]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:4]=[C:3]([F:2])[C:8]=1[NH2:9]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 668621544-(3,5-Difluoro-4-nitro-phenyl)-morpholine

Produkt 1

HCID 592443842,6-Difluoro-4-morpholin-4-yl-phenylamineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Concentrated hydrochloric acid (4.2 mL) was added slowly to a mixture of zinc dust (3.3 g) and 4-(3,5-difluoro-4-nitro-phenyl)-morpholine (2.49 g) in tetrahydrofuran (40 mL) cooled to 0° C. The reaction mixture was then stirred for 1 hour at 0° C. and 2 hours at 25° C. The reaction mixture was filtered through Celite (10 g), concentrated in vacuo and purified by flash chromatography to furnish 1.96 g (90% yield) of the title compound as a white solid. GC-MS (m/z) 214 (M+); tR=5.83. 1H NMR (500 MHz, DMSO-d6): 2.94 (t, 4H), 3.69 (t, 4H), 4.53 (s, 2H), 6.57 (m, 2H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite (10 g)
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-352230b7664c455eafef4da2e5dd40fe
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012962B2

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