Oxalic Acid → HCID 70373320, compound

HRID 1709813Notes

Reaction equation

HRID 1709813 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[O:12]([CH2:19][CH2:20][CH2:21]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>C(O)C>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([CH2:21][CH2:20][CH2:19][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 10340Sodium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 70373320HCID 70373320, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A mixture of ethyl isonipecotate (35.5 g 0.226 mole) 3-phenoxy-1-bromopropane (51.6 g, 0.24 mole) and sodium carbonate (25.4 g, 0.24 mole) in 500 ml of absolute ethanol was heated at reflux for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The solution was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give a liquid. The liquid was dissolved in absolute ethanol, and a solution of oxalic acid (~0.23 mole) in absolute ethanol was added. The product 73.43 g (87.7%) precipitated as a white, crystalline solid, m.p. 180°-181° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hr
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  5. dry with materialThe solution was dried over anhydrous sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give a liquid
  8. customThe product 73.43 g (87.7%) precipitated as a white, crystalline solid, m.p. 180°-181° C.

Sources & evidence

ORD record
ord-ad959af1b3e142ebb35f2a1e086ac695
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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