Oxalic Acid → HCID 12944322, compound

HRID 614542Notes

Reaction equation

HRID 614542 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH2:13]N2CCCCC2O)[C:10](=[O:12])[CH3:11])[CH2:4][CH2:3]1.C(O)(C(O)=O)=O>C(O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9](=[CH2:13])[C:10](=[O:12])[CH3:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 20550696HCID 20550696, compound

Product 1

HCID 12944322HCID 12944322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-[(4-Hydroxypiperidino)methyl]-4-(hydroxypiperidino)butan-2-one (1 g.) was dissolved in 8 ml. of ethyl alcohol and added to a cooled solution of oxalic acid anhydrous (0.9 g.) in 5 ml. of ethyl alcohol. After standing at 0° C. for five minutes, the resultant precipitate was filtered. The filtrate was stripped of solvent under reduced pressure and the residual oil taken up in a small volume of water, saturated with potassium carbonate and then extracted with ether. The ether solution was dried over anhydrous sodium sulphate, filtered and the filtrate stripped of ether. The residual oil, approx. 0.1 g., was characterized including a proton nuclear magnetic resonance spectrum in deuterated dimethylsulfoxide. There were two vinylic protons, at 5.9 and 6.1 ppm downfield from the reference tetramethylsilane.

Workup

  1. filtrationthe resultant precipitate was filtered
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried over anhydrous sodium sulphate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-93bb3983e1ce40609204b9672217317c
Source dataset
uspto-grants-1979_03
Patent number
US04145426

Reaction notes

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