Acetic Acid → 5-Methyl-2-{4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}cyclopent-2-en-1-one

HRID 1895990Notes

Reaction equation

HRID 1895990 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[CH3:17][CH:18]1[CH2:22][CH2:21][C:20](=O)[C:19]1=[O:24].C(O)(=O)C>C(O)C>[CH3:17][CH:18]1[C:19](=[O:24])[C:20]([N:14]2[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=3)[CH2:16][CH2:15]2)=[CH:21][CH2:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612093-Methyl-1,2-cyclopentanedioneHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 251819235-Methyl-2-{4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}cyclopent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the Compound of Example 3 (500 mg, 2.36 mmol), 3-methyl-1,2-cyclopentanedione (350 mg, 3.11 mmol), acetic acid (0.18 mL, 3.11 mmol) in ethanol (10 mL) was refluxed for 8 h. The reaction mixture was evaporated, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 85:15, affording the title product as a brown solid.

Workup

  1. temperaturewas refluxed for 8 h
  2. customThe reaction mixture was evaporated
  3. additionpoured into water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried on Na2SO4
  7. customevaporated to dryness in vacuo
  8. customto afford a residue, which
  9. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  10. washeluting with Petroleum Ether-EtOAc 85:15

Sources & evidence

ORD record
ord-6180f48b8c914cc6a17af5fac2fa0775
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…