Triethylamine → 1-{4-[2-(2-Fluorophenoxy)ethyl]piperazin-1-yl}-3-(3,4,5-trimethoxyphenyl)propan-1-one hydrochloride

HRID 1928547

Reaction equation

HRID 1928547 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[ClH:39].[F:40][C:41]1[CH:55]=[CH:54][CH:53]=[CH:52][C:42]=1[O:43][CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1.C(N(CC)CC)C>CN(C=O)C.O>[ClH:39].[F:40][C:41]1[CH:55]=[CH:54][CH:53]=[CH:52][C:42]=1[O:43][CH2:44][CH2:45][N:46]1[CH2:47][CH2:48][N:49]([C:15](=[O:17])[CH2:14][CH2:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:50][CH2:51]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 757711-HydroxybenzotriazoleHCID 7627031-[2-(2-Fluorophenoxy)ethyl]piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 672988021-{4-[2-(2-Fluorophenoxy)ethyl]piperazin-1-yl}-3-(3,4,5-trimethoxyphenyl)propan-1-one hydrochlorideYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(3,4,5-trimethoxyphenyl)propionic acid (0.36 g, 1.5 mmol), HOBt (0.24 g, 1.8 mmol), EDAC.HCl (0.34 g, 1.8 mmol) in DMF (4 mL) was added 1-[2-(2-fluoro-phenoxy)ethyl]piperazine (0.34 g, 1.5 mmol) and triethylamine (0.5 mL, 3.6 mmol). The mixture was then stirred at room temperature for a day, treated with water, and extracted with dichloromethane. The organic layer was washed with water and brine and then concentrated to dryness. The residue was dissolved in ethyl ether and was added with 2N HCl in ether (1 mL). The white solid was filtered and dried under vacuum to give the title compound (408 mg, 52%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in ethyl ether
  5. additionwas added with 2N HCl in ether (1 mL)
  6. filtrationThe white solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6695f11e100e428a9c8dd487a00325d2
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Linked notes

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