2-Methylacetanilide → HCID 54072114, compound

HRID 1447809Notes

Reaction equation

HRID 1447809 reaction equation
C([Li])CCC.[C:6]1([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:17][C:18]1[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=1[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]1>CCCCCC.O1CCCC1>[Cl:17][C:18]1[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=1[CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][C:25]([CH:14]([CH3:15])[C:13]([NH:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:16])([OH:28])[CH2:26][CH2:27]1

Participants

6

Reactant 3

HCID 121072-MethylacetanilideHCID 130615381-[2-(2-Chlorophenyl)ethyl]piperidin-4-oneHCID 178418339Butyllithium

Product 1

HCID 54072114HCID 54072114, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

48 cc of n-butyl-lithium in hexane are added dropwise at 0°, in an atmosphere of nitrogen with stirring, to a solution of 9 g of N-phenylpropionamide in 90 cc of anhydrous tetrahydrofuran. The mixture is stirred at 45°-48° for 21/2 hours and a solution of 10.5 g of N-o-chlorophenethyl-4-piperidone in 25 cc of anhydrous tetrahydrofuran is added dropwise within 50 minutes. The heating (oil bath) is removed and the reaction mixture is stirred for a further hour while cooling slowly. 10 cc of a 20% potassium carbonate solution are subsequently added to the reaction solution while stirring and cooling with ice, dilution is effected with ether and the organic phase is decanted, dried over magnesium sulphate and concentrated by evaporation at reduced pressure. The resulting crude compound is filtered over silica gel resulting crude compound is filtered over silica gel (eluant: chloroform containing 3% of methanol) and an equivalent amount of fumaric acid is added to the resulting title compound in ethanol whereby this crystallizes as hydrogen fumarate. The hydrogen fumarate form of the title compound has a M.P. of 159°-161°.

Workup

  1. customThe heating (oil bath) is removed
  2. stirringthe reaction mixture is stirred for a further hour
  3. temperaturewhile cooling slowly
  4. addition10 cc of a 20% potassium carbonate solution are subsequently added to the reaction solution
  5. stirringwhile stirring
  6. temperaturecooling with ice, dilution
  7. customthe organic phase is decanted
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated by evaporation at reduced pressure
  10. filtrationThe resulting crude compound is filtered over silica gel resulting crude compound
  11. filtrationis filtered over silica gel (eluant: chloroform containing 3% of methanol)
  12. additionan equivalent amount of fumaric acid is added to the resulting title compound in ethanol whereby
  13. customthis crystallizes as hydrogen fumarate

Sources & evidence

ORD record
ord-9e2e011fc95346a58fb59855d7842495
Source dataset
uspto-grants-1979_12
Patent number
US04178377

Reaction notes

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