Tetrahydrofuran → Methyl 4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}benzoate

HRID 534898Notes

Reaction equation

HRID 534898 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].Cl[C:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:21].C(N(CC)CC)C.O1CCCC1>O>[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:20]([C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)=[O:21])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751323Methyl 4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (0.5 g), methyl 4-(chlorocarbonyl)benzoate (397 mg), triethylamine (0.836 mL), and tetrahydrofuran (10 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (NH-silica gel, 90:10-50:50 hexane/ethyl acetate) to provide the title compound (628 mg, 96%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (NH-silica gel, 90:10-50:50 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b1e00b7b61354c4aab2a328494c72752
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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