Oxalic Acid → N-[3-(3-pyrrolidinomethylphenoxy)propyl]3-pyridinecarboxamide 1-oxide sesquioxalate

HRID 1981357Notes

Reaction equation

HRID 1981357 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[O:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl.[Cl-].[C:26]([OH:35])(=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[N+:29]([O-:33])[CH:28]=1.[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38]>C(Cl)Cl.C(O)C>[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[O:10][CH2:11][CH2:12][CH2:13][NH:14][C:26]([C:27]2[CH:28]=[N+:29]([O-:33])[CH:30]=[CH:31][CH:32]=2)=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5]1.[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[C:36]([OH:41])(=[O:40])[C:37]([OH:39])=[O:38].[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[O:10][CH2:11][CH2:12][CH2:13][NH:14][C:26]([C:27]2[CH:28]=[N+:29]([O-:33])[CH:30]=[CH:31][CH:32]=2)=[O:35])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 1049PyridineHCID 127974543-{3-[(Pyrrolidin-1-yl)methyl]phenoxy}propan-1-amineHCID 86740065HCID 86740065, compound

Product 1

HCID 131714194N-[3-(3-pyrrolidinomethylphenoxy)propyl]3-pyridinecarboxamide 1-oxide sesquioxalateYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.03 mol of 3-(3-pyrrolidinomethylphenoxy)propylamine and 0.095 mol of pyridine in 100 ml of methylene chloride, stirred at 0° C., 0.047 mol of nicotinic acid 1-oxide chloride hydrochloride is added portionwise, then the resulting mixture is stirred 1 hour at room temperature and the solvent is evaporated off under reduced pressure. The residue is taken up with N hydrochloric acid and the salts obtained are eliminated by filtration, then the solution is extracted 3 times with 100 ml of ethyl acetate and sodium hydroxide is added thereto up to a basic pH. The solution is extracted 4 times with 100 ml of ethyl acetate, the organic phase is dried over anhydrous sodium sulfate and the solvent is evaporated off under reduced pressure. The oil thus obtained is chromatographied on silica, and eluted with methanol, the fractions of the pure product are collected and the solution thus obtained is treated with a solution of oxalic acid in ethanol; the precipitate which forms is crystallized from ethanol to yield 3.5 g of N-[3-(3-pyrrolidinomethylphenoxy)propyl]3-pyridinecarboxamide 1-oxide sesquioxalate CM 57891A; m.p. 115°-116° C. Yield: 30% of the theoretical value.

Workup

  1. stirringthe resulting mixture is stirred 1 hour at room temperature
  2. customthe solvent is evaporated off under reduced pressure
  3. customthe salts obtained
  4. filtrationare eliminated by filtration
  5. extractionthe solution is extracted 3 times with 100 ml of ethyl acetate and sodium hydroxide
  6. additionis added
  7. extractionThe solution is extracted 4 times with 100 ml of ethyl acetate
  8. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  9. customthe solvent is evaporated off under reduced pressure
  10. customThe oil thus obtained
  11. washeluted with methanol
  12. customthe fractions of the pure product are collected
  13. customthe solution thus obtained
  14. customthe precipitate which forms is crystallized from ethanol

Sources & evidence

ORD record
ord-9bf27c0cc9d64a27976ca89951f887e6
Source dataset
uspto-grants-1985_04
Patent number
US04514408

Reaction notes

Loading…