Hydrogen Bromide → 1-Methyl-3-(3-methoxymethyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydropyridinium oxalate

HRID 1904297Notes

Reaction equation

HRID 1904297 reaction equation
[O-]CC.[Na+].[CH3:5][O:6][CH2:7][C:8](=[N:10][OH:11])[NH2:9].[CH3:12][N:13]1[CH2:18][C:17]([C:19]([O:21]C)=O)=[CH:16][CH2:15][CH2:14]1.Br.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>C(O)C.CCOCC>[C:24]([O-:29])(=[O:28])[C:25]([O-:27])=[O:26].[CH3:12][NH+:13]1[CH2:14][CH2:15][CH:16]=[C:17]([C:19]2[O:11][N:10]=[C:8]([CH2:7][O:6][CH3:5])[N:9]=2)[CH2:18]1.[CH3:12][NH+:13]1[CH2:14][CH2:15][CH:16]=[C:17]([C:19]2[O:21][N:10]=[C:8]([CH2:7][O:6][CH3:5])[N:9]=2)[CH2:18]1

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 971Oxalic AcidHCID 2230ArecolineHCID 2723922Sodium ethoxideHCID 4126736N'-hydroxy-2-methoxyethanimidamide

Product 1

HCID 230475141-Methyl-3-(3-methoxymethyl-1,2,4-oxadiazol-5-yl)-1,2,5,6-tetrahydropyridinium oxalate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of sodium ethoxide (prepared from sodium (180 mg;7.8 mmol)), distilled ethanol (20 ml), molecular sieves (5 g), and methoxymethylcarboxamide oxime (832 mg;8 mmol) were added. The mixture was stirred at room temperature for 10 min. whereafter arecoline, HBr (1.0 g;4.23 mmol) was added. The mixture was heated at 80° C. for 12 hours, filtered, and evaporated in vacuo. To the residue was added water (10 ml) and the mixture was extracted with ether (3×25 ml). The combined extracts were dried (MgSO4) and evaporated in vacuo. Upon disolving the residue in ethanol (99.9%)(5 ml) a solution of oxalic acid (350 mg;3.9 mmol) in ethanol (99.9%)(10 ml) was added. Addition of ether gave an analytically pure product in a yield of 500 mg (40%). M.P. 153°-154° C.

Workup

  1. additionwere added
  2. additionwas added
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. additionTo the residue was added water (10 ml)
  6. extractionthe mixture was extracted with ether (3×25 ml)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated in vacuo
  9. additionwas added
  10. customgave an analytically pure product in a yield of 500 mg (40%)

Sources & evidence

ORD record
ord-98dccf0661c549c4bd3ba4eeace91258
Source dataset
uspto-grants-1989_06
Patent number
US04837241

Reaction notes

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