Sodium Bicarbonate → Methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate hydrochloride

HRID 1877781Notes

Reaction equation

HRID 1877781 reaction equation
[ClH:1].Cl.[CH3:3][C:4]([CH3:16])([CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:5]([O:7][CH3:8])=[O:6].C(=O)(O)[O-].[Na+]>O>[ClH:1].[CH3:3][C:4]([CH3:16])([CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68155933Methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate dihydrochloride

Product 1

HCID 68156003Methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate hydrochlorideYield 84.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate dihydrochloride (112.0 g, 409.95 mmoles) in water (250 mL). Add solid sodium bicarbonate to give an aqueous layer of pH 4 and extract the mixture into a solution of 10% DCM in diethyl ether (300 mL) to remove some dark solid matter and some color. Discard the organic layer. Basify the aqueous phase to pH 8 with 2M aqueous sodium hydroxide solution, then saturate with solid sodium chloride. Extract into a 10% solution of isopropanol in chloroform. Add further 2M aqueous sodium hydroxide to maintain pH 8. Repeat the extraction into a 10% solution of isopropanol in chloroform. Continue the extraction process until 85% of the expected material has been recovered. Wash the isopropanol in chloroform solution with brine, dry over Na2SO4, filter and evaporate to give methyl 2,2-dimethyl-3-(piperazin-1-yl)propanoate hydrochloride (82.1 g % yield). MS (m/z): 201.1 (M+1).

Workup

  1. customto give an aqueous layer of pH 4
  2. extractionextract the mixture into a solution of 10% DCM in diethyl ether (300 mL)
  3. customto remove some dark solid matter
  4. concentrationBasify the aqueous phase to pH 8 with 2M aqueous sodium hydroxide solution, then saturate with solid sodium chloride
  5. extractionExtract into a 10% solution of isopropanol in chloroform
  6. additionAdd further 2M aqueous sodium hydroxide
  7. temperatureto maintain pH 8
  8. extractionRepeat the extraction into a 10% solution of isopropanol in chloroform
  9. customhas been recovered
  10. washWash the isopropanol in chloroform solution with brine
  11. dry with materialdry over Na2SO4
  12. filtrationfilter
  13. customevaporate

Sources & evidence

ORD record
ord-ce1899e366bc4483a8643a581e6623cd
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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