(3-Isopropoxy-4-nitrophenyl)(1-methylpiperidin-4-yl)amine → 2-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamine

HRID 518856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518856
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:8]=[CH:9][C:10]=1[N+:11]([O-])=O)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[CH:8]=[CH:9][C:10]=1[NH2:11])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 83005936(3-Isopropoxy-4-nitrophenyl)(1-methylpiperidin-4-yl)amine

Produkt 1

HCID 830025872-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamineAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.49 g of (3-isopropoxy-4-nitrophenyl)(1-methylpiperidin-4-yl)amine and 150 mg of 10% palladium-on-carbon in 60 ml of ethanol is hydrogenated at 25° C. under 1 bar for 3 h. The mixture is filtered on Clarcel and the Clarcel is rinsed with ethanol. The filtrate is concentrated to dryness under reduced pressure and the residue is purified by chromatography on a 70 g silica cartridge, elution being carried out with a 96.5/3/0.5 v/v/v dichloromethane/methanol/28% aqueous ammonia mixture at a flow rate of 50 ml/min, so as to obtain 0.9 g of 2-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamine in the form of a brown liquid.

Aufarbeitung

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with ethanol
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure
  4. customthe residue is purified by chromatography on a 70 g silica cartridge, elution

Quellen und Nachweise

ORD-Eintrag
ord-d4afad75af8144bda3a82c3fe9c381f1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115140B2

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