Methane → HCID 22099489, compound

HRID 1457588Notes

Reaction equation

HRID 1457588 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:21]=3[OH:32])=[O:18])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([O-])=O.CO.Cl.O1CCOCC1.C>ClCCl.[C].[Pd].O1CCOCC1>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([C:28]([CH3:30])([CH3:29])[CH3:31])[C:21]=3[OH:32])=[O:18])[CH2:15][CH2:16]2)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 22099399HCID 22099399, compound

Product 1

HCID 22099489HCID 22099489, compoundYield 60.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 680 mg of 2-{[4-(4-nitrophenyl)piperazin-1-yl]carbonylamino}-4-methoxy-6-tert-butylphenol hydrochloride, 30 ml of methanol and 30 ml of dioxane was added 100 mg of 10% palladium-carbon (Pd-C). The mixture was subjected to catalytic reduction for 4 hours by using a Parr's reduction apparatus. After removing the catalyst by filtration, the filtrate was condensed. The residue was dissolved in 10 ml of dichloromethane, and after adding 1 ml of 4N hydrogen chloride-dioxane solution, the mixture was treated with an activated charcoal. The treated mixture was evaporated to dryness under reduced pressure to give 210 mg of 2-{[4-(4-aminophenyl)piperazin-1-yl]carbonylamino}-4-methoxy-6-tert-butylphenol dihydrochloride as powder.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. customcondensed
  4. customThe treated mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1766d1bff4f94005a9649eb3b439dc2f
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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