Water → HCID 59559655, compound

HRID 1177895Notes

Reaction equation

HRID 1177895 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[NH2:12][CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]([F:32])([F:31])[F:30])[CH2:18][CH2:17]1)=[O:15].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH2:13][C:14](=[O:15])[N:16]2[CH2:17][CH2:18][N:19]([C:22](=[O:33])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:30])([F:32])[F:31])[CH2:20][CH2:21]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 59559655HCID 59559655, compoundYield 73.98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl benzoyl chloride (44 mg, 0.03 ml, 1.8 mmol) was added to a stirred a cold (0° C.) solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method described above)(100 mg, 0.28 mmol) and triethylamine (72 mg, 0.1 ml, 0.71 mmol) in DCM (5 mL) and stirring continued at room temperature for 3 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 50% EtOAc in Hexane as eluent) to afford 91 mg (73.98% yield 4-methyl-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 98.52%. 1H NMR (DMSO-d6): δ 8.54-8.42 (bs, 1H), 7.88-7.62 (m, 5H), 7.58-7.5 (bs, 1H), 7.3-7.22 (d, 2H), 4.2-4.1 (d, 2H), 3.8-3.5 (m, 4H), 3.5-3.4 (bs, 2H), 3.3-3.0 (bd, 2H), 2.3 (s, 3H)

Workup

  1. customprepared by the method
  2. extractionthe product was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto get the residue
  7. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 50% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-0e795986fc8f434aa03a11238d0ed950
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…