Triethylamine → Ethyl 3-oxo-3-[4-(4-oxo-1-piperidineyl)anilino]propanoate

HRID 1794916Notes

Reaction equation

HRID 1794916 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:24](=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(Cl)Cl>[O:31]=[C:24]([NH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][C:12](=[O:15])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Product 1

HCID 10780816Ethyl 3-oxo-3-[4-(4-oxo-1-piperidineyl)anilino]propanoateYield 7.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution, under N2 atmosphere, of 1-(4-amino-phenyl)-piperidin-4-one hydrochloride (which was obtained in Example 224) (10.0 g, 38 mmol), and triethylamine (15.35 g, 150 mmol) in methylene chloride (100 mL) was added ethyl 3-chloro-3-oxopropionate (6.32 g, 42 mmol). The reaction was stirred for 18 hours. The reaction mixture was concentrated down in vaco and purified by flash silica gel chromatography eluting with 1:1 ethyl acetate/hexanes to give an orange solid (0.86 g, 7%); 1H NMR (300 MHz, CDCl3) δ 1.32 (t, J=7.2 Hz, 3 H), 2.55 (t, J=6 Hz, 4 H), 3.46 (s, 2 H), 3.56 (t, J=6 Hz, 4 H), 4.22 (q, J=7.2 Hz, 2 H), 6.93(d, J=9.0 Hz, 2 H), 7.47(d, J=9.0 Hz, 2 H), 9.09 (s, 1 H); MS (ES) m/z: 305.3(MH+, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated down in vaco
  2. custompurified by flash silica gel chromatography
  3. washeluting with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-596851eeac604a2084c3cd09571e2c37
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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