Methanesulfonic Acid → 6,6-Diphenylpiperidin-2-one

HRID 1741771Notes

Reaction equation

HRID 1741771 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.[C:20]1([C:26]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH2:28][CH2:29][C:30]#[N:31])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-:39].[Na+]>C(OCC)(=O)C>[C:32]1([C:26]2([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:31][C:30](=[O:39])[CH2:29][CH2:28][CH2:27]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 123566855,5-Diphenylpent-4-enenitrile

Product 1

HCID 123566886,6-Diphenylpiperidin-2-oneYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 24. g (0.17 tool) of granular phosphorus pentoxide and 240.g (2.5 mol) of 98% methanesulfonic acid was maintained at 110 ° C. until all the solid dissolved (1 hour) . To this solution was added in portions over several minutes 12 g (0.05 mol) of 5,5-diphenyl-4-pentenenitrile. The resulting dark mixture was heated for 5 minutes longer and then carefully added to an ice-cooled vigorously stirred mixture of 1 liter of saturated aqueous sodium bicarbonate and 1 liter of ethyl acetate. The basic aqueous phase was extracted with 3×500 ml of fresh ethyl acetate, the organic layers were combined, washed with 2×500 ml of water, 1×500 ml brine, and dried over sodium sulfate. The resulting crude solid was recrystallized from toluene to give 8.5 g (66%) of 6,6-diphenyl-2-piperidinone as a white solid (mp 193°-196° C.) .

Workup

  1. dissolutiondissolved (1 hour)
  2. temperatureThe resulting dark mixture was heated for 5 minutes longer
  3. temperaturecooled vigorously stirred
  4. extractionThe basic aqueous phase was extracted with 3×500 ml of fresh ethyl acetate
  5. washwashed with 2×500 ml of water, 1×500 ml brine
  6. dry with materialdried over sodium sulfate
  7. customThe resulting crude solid was recrystallized from toluene

Sources & evidence

ORD record
ord-257e193d94ab4d17ac89d2332597577e
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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