Ethanol → HCID 12944322, compound

HRID 1413444Notes

Reaction equation

HRID 1413444 reaction equation
O[CH:2]1[CH2:7]CC[CH2:4][N:3]1[CH2:8][CH2:9][C:10](=[O:12])[CH3:11].[C:13](O)(C(O)=O)=O.[CH2:19]([OH:21])[CH3:20]>>[OH:21][CH:19]1[CH2:7][CH2:2][N:3]([CH2:8][C:9](=[CH2:13])[C:10](=[O:12])[CH3:11])[CH2:4][CH2:20]1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 971Oxalic AcidHCID 131712079HCID 131712079, compound

Product 1

HCID 12944322HCID 12944322, compound

Procedure

3-[(4-Hydroxypiperidino)methyl]-4-(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, approximately 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-56083d034f3942a8bca537331a6b31e1
Source dataset
uspto-grants-1981_02
Patent number
US04250184

Reaction notes

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