HCID 86698007, compound → HCID 86698006, compound

HRID 518851Notes

Reaction equation

HRID 518851 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:7][C:6]=1[N+:18]([O-])=O)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:7][C:6]=1[NH2:18])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86698007HCID 86698007, compound

Product 1

HCID 86698006HCID 86698006, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.57 g of 1-(4-isopropoxy-3-nitrophenyl)-4-methylpiperazine and 65 mg of 10% palladium-on-carbon in 200 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 methanol. The filtrate is concentrated to dryness under reduced pressure and the residue is purified by chromatography on a 25 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 0.32 g of 2-isopropoxy-5-(4-methylpiperazin-1-yl)phenylamine in the form of a brown solid.

Workup

  1. filtrationThe mixture is filtered on Clarcel
  2. washthe Clarcel is rinsed with methanol
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure
  4. customthe residue is purified by chromatography on a 25 g silica cartridge, elution

Sources & evidence

ORD record
ord-3faa214fdc6d44c9a5d59c1e9a831f63
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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