Hydrogen Bromide → 1,2,3,6-Tetrahydropyridine-4-carboxylic acid hydrobromide

HRID 1359486Notes

Reaction equation

HRID 1359486 reaction equation
C(OC([N:6]1[CH2:11][CH:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH2:8][CH2:7]1)=O)C.[BrH:17]>>[BrH:17].[NH:6]1[CH2:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 12549670Ethyl 1-ethoxycarbonyl-1,2,3,6-tetrahydropyridine-4-carboxylate

Product 1

HCID 125496741,2,3,6-Tetrahydropyridine-4-carboxylic acid hydrobromide

Procedure

To 104.4 g of ethyl 1-ethoxycarbonyl-1,2,3,6-tetrahydropyridine-4-carboxylate, 1500 g of 47% hydrobromic acid was added, and the mixture was heated under reflux for 100 hours. The reaction mixture was concentrated under reduced pressure to yield crude 1,2,3,6-tetrahydropyridine-4-carboxylic acid hydrobromide. The obtained crude 1,2,3,6-tetrahydropyridine-4-carboxylic acid hydrobromide was dissolved in a mixed solution of 0.48 l of dioxane and 0.48 l of a 2M aqueous solution of sodium hydroxide, and 105.2 g of tert-butyl bicarbonate were added thereto. The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 1.4 l of a 1M aqueous solution of potassium hydrogensulfate was poured thereinto. The precipitated crystals of 1-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid was obtained in an amount of 100.5 g by filtration.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 100 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af6c49061e104cceae3923c1cfc6a4ba
Source dataset
uspto-grants-2003_07
Patent number
US06600038B1

Reaction notes

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