2-Piperidone → HCID 178422639, compound

HRID 1673192Notes

Reaction equation

HRID 1673192 reaction equation
P(Cl)(Cl)(Cl)=O.[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=O.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([NH2:30])=[CH:25][C:24]=2[CH3:31])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([N:30]=[C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][NH:6]3)=[CH:25][C:24]=2[CH3:31])=[CH:21][CH:22]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 126652-PiperidoneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 598436854'-Tert-butyl-2,5-dimethylbiphenyl-4-amine

Product 1

HCID 178422639HCID 178422639, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 0.2 g (1.5 mmol) of phosphoric trichloride in 5 ml toluene was added to a mixture of 0.3 g (3.0 mmol) of piperidin-2-one, the exothermic reaction was stirred for 2 hrs at ambient temperature. Then a solution of 0.38 g (1.5 mmol) of 4′-tert-butyl-2,5-dimethylbiphenyl-4-amine in 5 ml of toluene was added and the reaction mixture was refluxed for 5 hrs. At ambient temperature 5 ml of a 10% aqueous solution of sodium hydroxide was added. Separation of the layers, extraction of the watery layer with 10 ml of toluene, drying over magnesium sulfate, concentration in vacuo and column chromatographic (gradient: cyclohexane->ethyl acetate) yielded 0.3 g (1.0 mmol) 63% of 4′-tert-butyl-2,5-dimethyl-N-[piperidin-2-ylidene]biphenyl-4-amine; log P (pH 2.3)=2.6.

Workup

  1. customthe exothermic reaction
  2. temperaturethe reaction mixture was refluxed for 5 hrs
  3. customSeparation of the layers, extraction of the watery layer with 10 ml of toluene
  4. dry with materialdrying over magnesium sulfate, concentration in vacuo and column chromatographic (gradient: cyclohexane->ethyl acetate)

Sources & evidence

ORD record
ord-9d213da6d4bf403cba4a3ef2378cba2a
Source dataset
uspto-grants-2011_08
Patent number
US07999137B2

Reaction notes

Loading…