Piperidine → HCID 14497180, compound

HRID 1780959Notes

Reaction equation

HRID 1780959 reaction equation
[C:1]1(C)[CH:6]=C[C:4]([NH:7][C:8]2C=CC=C[C:9]=2C=O)=[CH:3][CH:2]=1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([CH2:24][C:25](=O)[CH3:26])=[O:23].N1CCCCC1>C(O)C>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([C:24]1[C:8]([CH3:9])=[N:7][C:4]2[C:26]([CH:25]=1)=[CH:6][CH:1]=[CH:2][CH:3]=2)=[O:23]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 121681,3-Butanedione, 1-(2-furanyl)-HCID 127442602-(4-Methylanilino)benzaldehyde

Product 1

HCID 14497180HCID 14497180, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 410 mg (1.95 mmol) N-(p-tolyl)-o-aminobenzaldehyde 326 mg (2.15 mmol), (2-furoyl)acetone and 50 mg piperidine in 4 ml 95% ethanol was heated overnight under reflux. Removal of he volatile materials left a black, gummy oil which was taken up in dichloromethane and, after being washed with 3M NaOH, brine, and dried (MgSO4), purified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)] yielding 355 mg (1.50 mmol, 77%) product.

Workup

  1. temperatureunder reflux
  2. customRemoval of he volatile materials
  3. waitleft a black, gummy oil which
  4. washafter being washed with 3M NaOH, brine
  5. dry with materialdried (MgSO4)
  6. custompurified by flash chromatography [eluent, 3:2 pentane-diethyl ether (3:2)]

Sources & evidence

ORD record
ord-0c22f013146b4803aae89fe7bf0b0ee4
Source dataset
uspto-grants-1997_05
Patent number
US05631374

Reaction notes

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