Acetic Acid → HCID 53984378, compound

HRID 1440714Notes

Reaction equation

HRID 1440714 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[CH:17]=1.N1CCCCC1.C(O)(=O)C>C(OCC)(=O)C.C(O)C>[CH3:15][O:14][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[CH:22][C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 103713-PyridinecarboxaldehydeHCID 143453',4',5'-Trimethoxyacetophenone

Product 1

HCID 53984378HCID 53984378, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 3,4,5-trimethoxyacetophenone (5.25 g, 25 mmol), 3-pyridinecarboxaldehyde (2.35 mL, 25 mmol), piperidine (4.93 mL, 50 mmol), acetic acid (2.86 mL, 50 mmol) and ethanol (25 mL). Heat at reflux for 6 hour s, passing the distillate through a column of 3 Å molecular si eves (25 g). Dilute with ethyl acetate (600 mL), wash with IN sodium hydroxide (200 mL), then water, then saturated sodium chloride. Dry (MgSO4) and evaporate the solvent. Purify by silica gel chromatography (90% ethyl acetate/hexane). Recrystallize (methylene chloride/ethyl ether/hexane) to yield 1.75 g of the title compound; mp 137°-8° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 6 hour s
  3. washwash with IN sodium hydroxide (200 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent
  6. customPurify by silica gel chromatography (90% ethyl acetate/hexane)
  7. customRecrystallize (methylene chloride/ethyl ether/hexane)

Sources & evidence

ORD record
ord-f8ed3bc67abc4146ae73c63f72947c20
Source dataset
uspto-grants-1996_03
Patent number
US05500429

Reaction notes

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