Citric Acid → HCID 67662890, compound

HRID 962457Notes

Reaction equation

HRID 962457 reaction equation
Cl[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4]1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[C:24]([OH:36])(=[O:35])[CH2:25][C:26]([CH2:31][C:32]([OH:34])=[O:33])([C:28]([OH:30])=[O:29])[OH:27]>CCOCC>[C:24]([OH:36])(=[O:35])[CH2:25][C:26]([CH2:31][C:32]([OH:34])=[O:33])([C:28]([OH:30])=[O:29])[OH:27].[C:24]([OH:36])(=[O:35])[CH2:25][C:26]([CH2:31][C:32]([OH:34])=[O:33])([C:28]([OH:30])=[O:29])[OH:27].[O:11]([CH2:10][CH2:9][N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:4]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 8082PiperidineHCID 19085477HCID 19085477, compound

Product 1

HCID 67662890HCID 67662890, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-chloromethyl-1-(2-phenoxyethyl)piperidine (2.8 g) and piperidine (15 ml) was heated on a steam bath for 24 hours. The excess piperidine was removed under reduced pressure and the residue purified by azeotropic distillation with toluene. The residue was dissolved in ether/water and then basified to pH 14. The mixture was extracted with ether and the combined ether extracts yielded an oil which was dissolved in ether and acidified with ethereal citric acid to give a solid which was collected by filtration to give 1-(2-phenoxyethyl)-3-(piperidin-1-ylmethyl)piperidine dicitrate, m.p. 88°-89° C. (with decomposition).

Workup

  1. temperaturewas heated on a steam bath for 24 hours
  2. customThe excess piperidine was removed under reduced pressure
  3. distillationthe residue purified by azeotropic distillation with toluene
  4. dissolutionThe residue was dissolved in ether/water
  5. extractionThe mixture was extracted with ether
  6. customthe combined ether extracts yielded an oil which
  7. customto give a solid which
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-631b6478283741c587a8e80852b329e8
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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