Acetic Acid → HCID 15675405, compound

HRID 1461275Notes

Reaction equation

HRID 1461275 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[O:13][C:12]([C:14]([O:16]CC)=O)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:19](O)(=O)[CH3:20]>N1CCCCC1>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[O:13][C:12]([C:14]([N:5]3[CH2:20][CH2:19][CH2:2][CH2:3][CH2:4]3)=[O:16])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15675404HCID 15675404, compound

Product 1

HCID 15675405HCID 15675405, compoundYield 151.8%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

In 30 ml of piperidine was dissolved 7.4 g (29.25 mmol) of Compound s followed by addition of 2.7 g (45 mmol) of acetic acid, and the mixture was heated under reflux for 27 hours. After cooling, the excess piperidine was distilled off under reduced pressure and the residue was diluted with 300 ml of chloroform and washed with 3 portions of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Finally the residue was purified by silica gel column chromatography (acetone) to give 6.49 g (76.0%) of 1-[5-(4-hydroxypiperidinomethyl)-2-furancarbonyl]piperidine (Compound t) as light yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 27 hours
  3. temperatureAfter cooling
  4. distillationthe excess piperidine was distilled off under reduced pressure
  5. additionthe residue was diluted with 300 ml of chloroform
  6. washwashed with 3 portions of saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customFinally the residue was purified by silica gel column chromatography (acetone)

Sources & evidence

ORD record
ord-d334ac3f261f4bcd82e19cf65dc5e981
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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