Carbon Dioxide → HCID 20296622, compound

HRID 1389461Notes

Reaction equation

HRID 1389461 reaction equation
[CH2:1]([S:4]([CH2:7][C:8](O)=O)(=[O:6])=[O:5])[CH2:2][CH3:3].[OH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C=O.[C:20](=O)=O>O.O1CCOCC1>[CH2:1]([S:4]([C:7](=[CH2:8])[CH2:20][N:15]1[CH2:16][CH2:17][CH:12]([OH:11])[CH2:13][CH2:14]1)(=[O:5])=[O:6])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 712FormaldehydeHCID 79341Piperidin-4-olHCID 20296628(Propane-1-sulfonyl)acetic acid

Product 1

HCID 20296622HCID 20296622, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
57 °C

Procedure

In a 1 l. 3-neck round bottom flask, under a nitrogen atmosphere, 13 g. (0.078 mole) of n-propylsulfonylacetic acid was dissolved in 75 ml. of dioxane. There was then added with good stirring a solution of 7.89 g. (0.078 mole) of 4-hydroxypiperidine in 75 ml. of dioxane and 5 ml. of water (obtained by warming to 40° C.). The almost clear solution was kept at 30° C. and over a 10 minute period 12.7 g. of a 37% aqueous formaldehyde solution (0.156 mole) was dripped in. After complete addition there was gradual warming of the reaction mixture to 50° C. with carbon dioxide evolution. The temperature rose to 57° C. with vigorous gas evolution; and the reaction mixture was maintained at 57° C. for 4 hours, followed by stirring for 12 hours at 20°-25° C. The solvents were removed in vacuo; the residual oil was taken up in methylene chloride, washed well with water, dried over anhydrous sodium sulfate, again concentrated, then taken up in ether (120 m.), washed twice with 10 ml. of water, dried over anhydrous sodium sulfate; and the solvent was removed to leave 7 g. of the product as an oil.

Workup

  1. additionThere was then added
  2. additionAfter complete addition there
  3. customrose to 57° C. with vigorous gas evolution
  4. stirringby stirring for 12 hours at 20°-25° C
  5. customThe solvents were removed in vacuo
  6. washwashed well with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationagain concentrated
  9. washwashed twice with 10 ml
  10. dry with materialof water, dried over anhydrous sodium sulfate
  11. customand the solvent was removed
  12. customto leave 7 g

Sources & evidence

ORD record
ord-a0c6cf64de8a46fc9135c20ca7d32efb
Source dataset
uspto-grants-1981_01
Patent number
US04244963

Reaction notes

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