Water → HCID 66792770, compound

HRID 535004Notes

Reaction equation

HRID 535004 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-])=O.C(N(CC)CC)C.O>O1CCCC1.CO.[C].[Pd]>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:26]([C:25]2[CH:29]=[CH:30][C:22]([NH2:19])=[CH:23][CH:24]=2)=[O:27])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66792770HCID 66792770, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.00 g, 3.42 mmol), 4-nitrobenzoyl chloride (0.761 g, 4.1 mmol) and triethylamine (1.67 mL, 12.0 mmol) in tetrahydrofuran (25 mL) was stirred at room temperature for overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a solid. A mixture of the obtained solid and 10% of palladium-carbon (100 mg) in tetrahydrofuran (30 mL) and methanol (100 mL) was stirred at room temperature under hydrogen atmosphere (5 atm). After being stirred for 3 h, the reaction mixture was filtrated and concentrated to purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 0:100) and the title compound was obtained as a solid (1.28 g, quant.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid
  7. stirringwas stirred at room temperature under hydrogen atmosphere (5 atm)
  8. stirringAfter being stirred for 3 h
  9. filtrationthe reaction mixture was filtrated
  10. concentrationconcentrated
  11. customto purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 0:100)

Sources & evidence

ORD record
ord-a5ae6296a1c04d2f8bf237da24b118e5
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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