Hydrochloric Acid → HCID 53950422, compound

HRID 1646920Notes

Reaction equation

HRID 1646920 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].C([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=O.[C:23](=O)([O-])O.[Na+].Cl>CO.S(=O)(=O)(O)O>[CH3:23][O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1781211-Bromoundecanoic acidHCID 821911-PiperazinecarboxaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 53950422HCID 53950422, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

A 26.5 g (0.1 mole) quantity of 11-bromoundecanoic acid was dissolved in 300 ml of methanol, and 5 to 6 drops of sulfuric acid was added thereto and the mixture was stirred at room temperature for 24 hours and concentrated. A 500 ml quantity of ethyl acetate was added to the residue and the mixture was washed sequentially with 100 ml of water and 100 ml of a brine, followed by drying over anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure and the residue was dissolved in 200 ml of dimethylformamide. To the solution were added 11.4 g (0.1 mole) of formylpiperazine and 18.5 g (0.22 mole) of sodium hydrogen carbonate. The mixture was stirred at 80° C. for 3 hours and concentrated under reduced pressure. A 500 ml quantity of ethyl acetate was added to the residue and the mixture was washed sequentially with 100 ml of water and 100 ml of a brine, followed by drying over anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure. To the residue were added 300 ml of methanol and 50 ml of concentrated hydrochloric acid, and the mixture obtained was refluxed for 3 hours. The solvent was evaporated under reduced pressure and the precipitated white crystals were washed with acetone, giving 25 g (yield: 70%) of 11-(1-piperazyl)undecanoic acid methyl ester as the hydrochloride.

Workup

  1. concentrationconcentrated
  2. additionA 500 ml quantity of ethyl acetate was added to the residue
  3. washthe mixture was washed sequentially with 100 ml of water and 100 ml of a brine
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. customEthyl acetate was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in 200 ml of dimethylformamide
  7. stirringThe mixture was stirred at 80° C. for 3 hours
  8. concentrationconcentrated under reduced pressure
  9. additionA 500 ml quantity of ethyl acetate was added to the residue
  10. washthe mixture was washed sequentially with 100 ml of water and 100 ml of a brine
  11. dry with materialby drying over anhydrous magnesium sulfate
  12. customEthyl acetate was evaporated under reduced pressure
  13. additionTo the residue were added 300 ml of methanol and 50 ml of concentrated hydrochloric acid
  14. customthe mixture obtained
  15. temperaturewas refluxed for 3 hours
  16. customThe solvent was evaporated under reduced pressure
  17. washthe precipitated white crystals were washed with acetone

Sources & evidence

ORD record
ord-15e5efba7e8c4b5e975af0ca2b3ae11c
Source dataset
uspto-grants-1993_01
Patent number
US05182284

Reaction notes

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