2'-Hydroxyacetophenone → 1'-Benzoylspiro[chroman-2,4'-piperidin]-4-one

HRID 1781370Notes

Reaction equation

HRID 1781370 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])(=[O:3])[CH3:2].[C:11]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCC1>CO>[C:11]([N:19]1[CH2:24][CH2:23][C:22]2([CH2:2][C:1](=[O:3])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:10]2)[CH2:21][CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 31268PyrrolidineHCID 90583N-Benzoyl-4-piperidone

Product 1

HCID 72605101'-Benzoylspiro[chroman-2,4'-piperidin]-4-oneYield 68,961.602%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-acetylphenol (5 g, 0.037 mmol), 1-benzoyl-4-piperidone (7.5 g, 0.037 mmol), pyrrolidine (2.6 g, 0.037 mol) and CH3OH (50 ml) was heated at reflux for 8 hours. After cooling to room temperature overnight, the solid was filtered to yield 8.2 g of 1'-benzoyl-3,4-dihydro-spiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one. The mother liquor was concentrated to dryness and the residue triturated with ether to yield an additional 1.7 g (83% total yield).

Workup

  1. temperatureat reflux for 8 hours
  2. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-11292f8d3ee3493ab3e125d923f45655
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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