Pyrrolidine → 1'-Benzoyl-3,4-dihydro-6-methoxy-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one

HRID 1591224Notes

Reaction equation

HRID 1591224 reaction equation
N1CCCC1.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16].[C:18]([N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[C:18]([N:26]1[CH2:31][CH2:30][C:29]2([CH2:16][C:15](=[O:17])[C:8]3[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=3[O:6]2)[CH2:28][CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-oneHCID 90583N-Benzoyl-4-piperidone

Product 1

HCID 190454151'-Benzoyl-3,4-dihydro-6-methoxy-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-oneYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyrrolidine (8.35 ml, 7.11 g, 0.1 mol) was added to a suspension of 2'-hydroxy-5'-methoxyacetophenone (16.62 g, 0.1 mol) in methanol (100 ml). The mixture was stirred for 10 minutes, then 1-benzoyl-4-piperidone (20.32 g, 0.1 mol) was added and the mixture was heated under reflux for 7 hr. The mixture was cooled and the solvent was evaporated under reduced pressure. Water (400 ml) was added and the mixture was extracted with ethyl acetate (3×400 ml). The combined organic fractions were evaporated under reduced pressure and the residue was recrystallized from methanol to give the ketone as a pale yellow solid (29.54 g, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 hr
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. additionWater (400 ml) was added
  6. extractionthe mixture was extracted with ethyl acetate (3×400 ml)
  7. customThe combined organic fractions were evaporated under reduced pressure
  8. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-a28ecb9a8d6442b2ab1e6788b1809b07
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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