Potassium Hydroxide → HCID 22561850, compound

HRID 1839670Notes

Reaction equation

HRID 1839670 reaction equation
C(OC([C:6]1[NH:7][C:8]([CH3:19])=[C:9]([C:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=2)[C:10]=1[CH3:11])=O)C.[OH-].[K+]>O.CO>[CH3:19][C:8]1[NH:7][CH:6]=[C:10]([CH3:11])[C:9]=1[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20761743HCID 20761743, compound

Product 1

HCID 22561850HCID 22561850, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3,5-dimethyl-4-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-pyrrole-2-carboxylic acid ethyl ester (1.02 g, 3.9 mmol), KOH (0.287 g, 5.1 mmol) in water (5 mL) and methanol (10 mL) was heated to reflux under nitrogen for 3 days. The cooled reaction was extracted with ethyl acetate (3×), dried and concentrated to give 380 mg of 4-(2,4-dimethyl-1H-pyrrol-3-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine. The aqueous layer was adjusted to pH 7, the resulted precipitate was collected by filtration, washed with water to give 380 mg of 4-(2,4-dimethyl-1H-pyrrol-3-yl)-1-methyl-1,2,3,6-tetrahydro-pyridine and 480 mg of 3,5-dimethyl-4-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-pyrrole-2-carboxylic acid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 3 days
  3. customThe cooled reaction
  4. extractionwas extracted with ethyl acetate (3×)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eda67bbaa48e43d1bd6006f280db7144
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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