Potassium Carbonate → HCID 11279224, compound

HRID 1169113Notes

Reaction equation

HRID 1169113 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

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 9 for 3 hours. Ice water was added, followed by extraction with ethyl ether; the extract was washed with saline, dried over magnesium sulfate and 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 for 1 hour. 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, dried over magnesium sulfate and 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 over magnesium sulfate
  4. concentrationconcentrated 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 for 1 hour
  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 over magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customthe crystal precipitate was collected
  14. washwashed with ethyl ether
  15. customdried

Sources & evidence

ORD record
ord-6f2b683143614465b1050768a9dea4c6
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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