Hydrochloric Acid → 1-Methyl-1,2,3,6-tetrahydropyridin-1-ium-5-carboxylic acid;chloride
Reaction equation
[CH3:1][N:2]1[CH2:7][C:6]([C:8]([O:10]C)=[O:9])=[CH:5][CH2:4][CH2:3]1.[ClH:12].Cl>C(O)C>[CH3:1][NH+:2]1[CH2:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH2:4][CH2:3]1.[Cl-:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
In a 250 ml flask equipped with a magnetic stirrer and a condenser, arecoline hydrochloride (4 g; 20.9 mmol) is added to a solution of 50 ml of 95% ethanol and 60 ml of concentrated HCl. The mixture is heated at 100° C. for 12 hours then at reflux for 6 hours. The solvents are evaporated off under reduced pressure leaving a solid residue. The residue is recrystallized from a 95% ethanol/ether mixture in order to produce 1.69 g of product (Yield=46%) in the form of white crystals.
Workup
- customIn a 250 ml flask equipped with a magnetic stirrer and a condenser
- temperatureat reflux for 6 hours
- customThe solvents are evaporated off under reduced pressure
- customleaving a solid residue
- customThe residue is recrystallized from a 95% ethanol/ether mixture in order
Sources & evidence
- ORD record
- ord-fad818f96b7040cabd0e588cf5e3fc47
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745413B2
Reaction notes
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