HCID 86698009, compound → HCID 86698008, compound

HRID 518854Notes

Reaction equation

HRID 518854 reaction equation
[CH:1]([O:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:6]=1[N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([O:4][C:5]1[C:6]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:7][CH:8]=[CH:9][C:10]=1[NH2:11])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86698009HCID 86698009, compound

Product 1

HCID 86698008HCID 86698008, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.80 g of 1-(2-isopropoxy-3-nitrophenyl)-4-methylpiperazine and 91 mg of 10% palladium-on-carbon in 300 ml of ethanol is hydrogenated at 25° C. under 1 bar for 22 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 50 g silica cartridge, elution being carried out with pure dichloromethane and then successively with 98/2 and 95/5 v/v dichloromethane/methanol mixtures at a flow rate of 30 ml/min, so as to obtain 0.60 g of 2-isopropoxy-3-(4-methylpiperazine-1-yl)phenylamine in the form of a yellow powder.

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 50 g silica cartridge, elution

Sources & evidence

ORD record
ord-0b53aedc92ab4972a1105404d1db290c
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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