Potassium Iodide → 4-(4-hydroxy-4-(2-(4-hydroxybutyloxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide

HRID 279082Notes

Reaction equation

HRID 279082 reaction equation
[OH:1][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4][CH2:3]1.Br[CH2:36][CH2:37][CH2:38][CH2:39][O:40]C(=O)C.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C(Cl)(Cl)Cl.O>[OH:1][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 102263704-[4-(2-hydroxyphenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenyl-N,N-dimethylbutanamide

Product 1

HCID 102087204-(4-hydroxy-4-(2-(4-hydroxybutyloxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamideYield 24.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 10 mL of anhydrous dimethylformamide was dissolved 920 mg (2 mmol) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide. To the resulting solution were added 585 g (3 mmol) of 4-bromobutylacetate, 414 mg (3 mmol) of potassium carbonate and a small amount of potassium iodide. The resulting mixture was stirred under heating at 80° C. for 4 hours. After cooling, the reaction mixture was poured into water, followed by extraction with ethyl acetate, washing with water and drying. The residue obtained by distilling off the solvent under reduced pressure was dissolved in 15 mL of methanol. To the resulting solution was added 3 mL of a 1N aqueous solution of sodium hydroxide, followed by stirring at room temperature for 1 hour. From the reaction mixture, the solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in chloroform. The resulting solution was washed with water and dried. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 260 mg (yield: 24.5%) of 4-(4-hydroxy-4-(2-(4-hydroxybutyloxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 34) was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with water
  4. customdrying
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. dissolutionwas dissolved in 15 mL of methanol
  8. additionTo the resulting solution was added 3 mL of a 1N aqueous solution of sodium hydroxide
  9. stirringby stirring at room temperature for 1 hour
  10. distillationFrom the reaction mixture, the solvent was distilled off under reduced pressure
  11. customThe residue thus obtained
  12. washThe resulting solution was washed with water
  13. customdried
  14. customThe residue obtained
  15. distillationby distilling off the solvent under reduced pressure
  16. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-162cb439b3c54407abc490dbbad526e4
Source dataset
uspto-grants-2002_03
Patent number
US06362203B1

Reaction notes

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