Potassium Hydroxide → Acetamide, N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-

HRID 847745Notes

Reaction equation

HRID 847745 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].[NH:17]([CH2:21][CH2:22][CH2:23]Br)[C:18]([CH3:20])=[O:19]>C(O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:23][CH2:22][CH2:21][NH:17][C:18](=[O:19])[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 8269741-(3-Hydroxybenzyl)piperidineHCID 11830025N-(3-bromopropyl)acetamide

Product 1

HCID 9971484Acetamide, N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-Yield 70.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

191 mg of 3-(1-piperidinylmethyl)phenol was dissolved in 10 ml of ethanol, and 116 mg of potassium hydroxide was added. The mixture was heated under reflux, and a solution of 360 mg of 3-acetamino-1-bromopropane in 3 ml of ethanol. The reaction mixture was heated under reflux for 8 hours, and the solvent was distilled off under reduced pressure. Water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 205 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]acetamide as an oil. The resulting product coincided with the product obtained in Example 2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 8 hours
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionWater was added
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by TLC (developing solvent: chloroform/methanol=9/l)

Sources & evidence

ORD record
ord-4d72ee2b4fe04a1684558eed2b18c234
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

Loading…