Potassium Carbonate → HCID 11279224, compound

HRID 1067579Notes

Reaction equation

HRID 1067579 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:28][CH2:27][CH2:26][CH2:25][OH:24])[CH2:11][CH2:10]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 11279224HCID 11279224, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.05 g of 4-(diphenylmethoxy)piperidine was dissolved in 10 ml of N,N-dimethylformamide; 0.57 ml of 4-bromobutyl acetate and 652 mg of potassium carbonate were added, followed by stirring at 50° C. for 3 hours. Ice water was added, followed by extraction with ethyl ether; the extract was washed with saline and dried with magnesium sulfate. After the dry product was concentrated under reduced pressure, the residue was dissolved in 15 ml of ethanol; 8 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by stirring at room temperature. After the mixture was concentrated under reduced pressure, the residue was neutralized with 1 N hydrochloric acid, followed by extraction with ethyl acetate; the extract was washed with saline and dried with magnesium sulfate. After the dry product was concentrated under reduced pressure, the crystal precipitate was collected, washed with ethyl ether and dried to yield 1.21 g of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl ether
  2. washthe extract was washed with saline
  3. dry with materialdried with magnesium sulfate
  4. concentrationAfter the dry product was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 15 ml of ethanol
  6. addition8 ml of a 1 N aqueous solution of sodium hydroxide was added
  7. stirringby stirring at room temperature
  8. concentrationAfter the mixture was concentrated under reduced pressure
  9. extractionfollowed by extraction with ethyl acetate
  10. washthe extract was washed with saline
  11. dry with materialdried with magnesium sulfate
  12. concentrationAfter the dry product was concentrated under reduced pressure
  13. customthe crystal precipitate was collected
  14. washwashed with ethyl ether
  15. customdried

Sources & evidence

ORD record
ord-15134c2f18484f459bd7bb54b848f979
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

Loading…