Acetamide → HCID 20065178, compound

HRID 359547Notes

Reaction equation

HRID 359547 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:10]#[CH:11])[CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N)(=[O:20])C.[OH-].[K+]>C(O)(=O)C.C(OC(=O)C)(=O)C.C(Cl)Cl.CO>[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:10](=[O:20])[CH3:11])[CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

8

Reactant 3

HCID 178AcetamideHCID 14797Potassium HydroxideHCID 20065175HCID 20065175, compound

Product 1

HCID 20065178HCID 20065178, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 114.5 g (0.5 mole) of 2-hydroxy-2-phenyl-1 piperidino-3-butyne in 500 mL of acetic acid and 50 mL of acetic anhydride is added 160 g (0.5 mole) of mercuric acetate. After being stirred overnight at room temperature, the mixture is poured into a 1-L round bottomed flask equipped with an overhead stirrer and diluted with 500 mL of methylene chloride. To this is added 86 g (1.18 mole) of acetamide and 1 L of celite. After being stirred overnight, the mixture is filtered through a large pad of celite. The filtrate is washed three times with water, twice with a 5% aqueous solution of sodium hydroxide, and once with brine. After the organic layer is dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure The residue is dissolved in a solution of 35 g (0.57 mole) of potassium hydroxide in 750 mL of methanol and heated to reflux for 4 hours; the solution is cooled and then poured onto ice. The mixture is extracted four times with methylene chloride. The organic layers are combined, washed four times with water, once with brine dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. Distillation of the residue gives 2-hydroxy-2-phenyl-1-piperidino-3-butanone.

Workup

  1. additionthe mixture is poured into a 1-L round bottomed flask
  2. customequipped with an overhead stirrer
  3. stirringAfter being stirred overnight
  4. filtrationthe mixture is filtered through a large pad of celite
  5. washThe filtrate is washed three times with water
  6. dry with materialAfter the organic layer is dried over anhydrous magnesium sulfate
  7. customthe solvent is removed under reduced pressure The residue
  8. temperatureheated
  9. temperatureto reflux for 4 hours
  10. temperaturethe solution is cooled
  11. additionpoured onto ice
  12. extractionThe mixture is extracted four times with methylene chloride
  13. washwashed four times with water
  14. dry with materialonce with brine dried over anhydrous magnesium sulfate
  15. customthe solvent removed under reduced pressure
  16. distillationDistillation of the residue

Sources & evidence

ORD record
ord-d32f11c94a8540bcb0f7141af1b29cfa
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

Loading…