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

HRID 518856Notes

Reaction equation

HRID 518856 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

HCID 830025872-isopropoxy-N4-(1-methylpiperidin-4-yl)benzene-1,4-diamineYield 67.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d4afad75af8144bda3a82c3fe9c381f1
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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