2-Piperidone → HCID 86683077, compound

HRID 1497261Notes

Reaction equation

HRID 1497261 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].Cl[C:11]1[C:20]([C:21]#[N:22])=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Cl:29])[CH:17]=2)[N:12]=1>C1(C)C=CC=CC=1.O>[Cl:29][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])[C:20]([C:21]#[N:22])=[C:19]2[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 126652-PiperidoneHCID 24758Sodium hydrideHCID 86682946HCID 86682946, compound

Product 1

HCID 86683077HCID 86683077, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of sodium hydride (31.5 mg, 55% in mineral oil, 0.723 mmol) in toluene (4 ml) was added piperidin-2-one (133 mg, 1.34 mmol) followed by 2,6-dichloro-4-phenyl-quinoline-3-carbonitrile (prepared as described in example 27 step B) (200 mg, 0.669 mmol) and the mixture was heated to 100° C. for 6 h. The reaction mixture was cooled to room temperature, diluted with water and extracted twice with DCM and twice with EtOAc. The combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was triturated with cold diethyl ether to afford the title compound (157 mg, 62%) as light yellow solid. MS (ESI): 362.3 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted twice with DCM and twice with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe remaining residue was triturated with cold diethyl ether

Sources & evidence

ORD record
ord-82847960404149e98e1ec39b6e388063
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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