Acetic Acid → HCID 69749406, compound

HRID 585490Notes

Reaction equation

HRID 585490 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([C:21](O)=O)[C:18]([OH:20])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCOCC1.C(O)(=O)C.C=O>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]([C:18]([OH:20])=[O:19])=[CH2:21])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 22337492HCID 22337492, compound

Product 1

HCID 69749406HCID 69749406, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Benzyloxycarbonyl-piperidin-4-yl)-malonic acid (18.06 g) was dissolved in tetrahydrofuran (140 ml) and morpholine (4.95 ml) followed by acetic acid (6.43 ml) was added, forming a white precipitate. Formaldehyde (4.56 g) was added, causing the precipitate to disappear, and the mixture heated to reflux for 4 h. The solvent was evaporated, diethyl ether (50 ml) added and the mixture extracted with water (3×60 ml). The aqueous was acidified to pH=3 with citric acid and extracted with diethyl ether (3×30 ml). The combined organic extracts were washed with water (40 ml) and brine (40 ml), dried (Na2SO4), filtered and the solvent removed under reduced pressure to give the title compound (16.65 g) as a mixture containing approximately 10% of the acid starting material.

Workup

  1. additionwas added
  2. customforming a white precipitate
  3. temperaturethe mixture heated
  4. temperatureto reflux for 4 h
  5. customThe solvent was evaporated
  6. additiondiethyl ether (50 ml) added
  7. extractionthe mixture extracted with water (3×60 ml)
  8. extractionextracted with diethyl ether (3×30 ml)
  9. washThe combined organic extracts were washed with water (40 ml) and brine (40 ml)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d77246febee242a290cffa9b76847ec1
Source dataset
uspto-grants-2005_08
Patent number
US06933306B2

Reaction notes

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