Hydrochloric Acid → 1-[(Prop-2-en-1-yloxy)carbonyl]-1,2,3,6-tetrahydropyridine-4-carboxylic acid

HRID 1385890Notes

Reaction equation

HRID 1385890 reaction equation
Cl.[C:2]([OH:10])(=[O:9])[C:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19].Cl>O.ClCCl>[CH2:21]([O:20][C:18]([N:6]1[CH2:7][CH2:8][C:3]([C:2]([OH:10])=[O:9])=[CH:4][CH2:5]1)=[O:19])[CH:22]=[CH2:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 18052Allyl chloroformateHCID 155107Isoguvacine Hydrochloride

Product 1

HCID 108567621-[(Prop-2-en-1-yloxy)carbonyl]-1,2,3,6-tetrahydropyridine-4-carboxylic acidYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1,2,5,6-Tetrahydroisonicotinic acid hydrochloride (150 g, 0.92 mol) is added to an aqueous solution of sodium carbonate (194 g, 1.83 mol) in water (920 ml), and thereto is added dropwise 2-propenyl chloroformate (116 g, 0.96 mol) under ice-cooling over a period of one hour. After the addition, the mixture is further stirred under icecooling for five hours. Separately, conc. hydrochloric acid (191 g) and dichloromethane (1000 ml) are cooled, and thereto is added dropwise the above reaction mixture in portions. The mixture is separated, and the aqueous layer is extracted twice with dichloromethane. The organic layers are combined, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure to remove the solvent to give 1-(2-propenyloxycarbonyl)-1,2,5,6-tetrahydro-isonicotinic acid (198.9 g, quant.) as a white solid.

Workup

  1. temperaturecooling over a period of one hour
  2. additionAfter the addition
  3. additionis added dropwise the above reaction mixture in portions
  4. customThe mixture is separated
  5. extractionthe aqueous layer is extracted twice with dichloromethane
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-5011fed284c6434287798f43bdc64543
Source dataset
uspto-grants-2001_07
Patent number
US06265396B1

Reaction notes

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