Ammonia → 3,3-Diphenyl-2-pyrrolidinone

HRID 1667061

Reaction equation

HRID 1667061 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][O:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:19]>[Cl-].[Zn+2].[Cl-].C(O)C>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:19][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 70393Dihydro-3,3-diphenyl-2(3H)-furanone

Product 1

HCID 2382533,3-Diphenyl-2-pyrrolidinone

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
225 °C

Procedure

3,3-Diphenyldihydrofuran-2(3H)-one (3.98 g, 16.70 mmol) and zinc chloride (0.080 g) were placed in an autoclave. Ammonia (8 mL) was added, and the reactor was sealed and heated at 225° C. for 21 hours under an argon atmosphere at an equilibrium pressure of 800 pounds per square inch. The vessel was cooled, the ammonia was vented, and a mixture of solids was obtained. The solid was treated with ethanol (100 mL), filtered and concentrated. Silica gel chromatography eluting with 5% methanol/dichloromethane gave the title compound. MS (DCI+) m/z 238.1 (M+H)+.

Workup

  1. customthe reactor was sealed
  2. temperatureThe vessel was cooled
  3. additiona mixture of solids
  4. customwas obtained
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography eluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-11a05090fd12422c8e019d8a70dd8476
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Linked notes

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