Water → 1-[(4-Bromophenyl)carbonyl]-4-(2-tert-butylphenyl)piperazine

HRID 535024Notes

Reaction equation

HRID 535024 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].[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C.O>O1CCCC1>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:14][CH2:15]2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 667508841-[(4-Bromophenyl)carbonyl]-4-(2-tert-butylphenyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (10.0 g, 34.3 mmol), 4-bromobenzoyl chloride (8.2 g, 37.4 mmol) and triethylamine (16.7 mL, 120.0 mmol) in tetrahydrofuran (200 mL) was stirred at room temperature for 16 h. 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 purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 50:50 to 0:100). Solvent was removed to obtain a solid (14.2 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 purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 50:50 to 0:100)
  7. customSolvent was removed
  8. customto obtain a solid (14.2 g, quant.)

Sources & evidence

ORD record
ord-152180fdf31b407996c90b122f6e2224
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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