Water → 5-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]pent-3-yn-2-one

HRID 1895978Notes

Reaction equation

HRID 1895978 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][C:13](=[CH:16][C:17]#[CH:18])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:19](Cl)(=[O:21])[CH3:20].C(N(CC)CC)C.O>C1COCC1.[Cu]I>[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][C:13](=[CH:16][C:17]#[C:18][C:19](=[O:21])[CH3:20])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866273353-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine

Product 1

HCID 251817925-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]pent-3-yn-2-oneYield 28.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Compound 1c (52 mg; 0.213 mmol), acetyl chloride (46 mL, 0.647 mmol), bis(triphenyl)palladium(II)dichloride (4.49 mg, 0.0064 mmol) and copper (I) iodide (1.62 mg, 0.085 mmol) in anhydrous THF (5 mL), was added triethylamine (85 μL, 0.61 mmol) and the reaction mixture was stirred, in a closed vessel, at 60° C. for 5 h, cooled to r.t. poured into water and extracted with EtOAc. The combined extracts were washed with NaOH 0.1N, water, dried over Na2SO4 and evaporated to dryness in vacuo. Purification by flash chromatography (EtOAc—Petroleum Ether 25:75), afforded 17.5 mg of the title product.

Workup

  1. temperaturecooled to r.t.
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with NaOH 0.1N, water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customPurification by flash chromatography (EtOAc—Petroleum Ether 25:75)

Sources & evidence

ORD record
ord-b52bbee1dcd24fabb5ffce112be5913d
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…