Acetic Acid → HCID 69749406, compound

HRID 1634196Notes

Reaction equation

HRID 1634196 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-c6a46278d8f84c84ab051d055c2425a1
Source dataset
uspto-grants-2003_01
Patent number
US06506773B2

Reaction notes

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