Tetrahydrofuran → 5-(Piperidin-1-yl)pyrazine-2-carboxylic acid

HRID 340090Notes

Reaction equation

HRID 340090 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][N:6]=1)=[O:4].[OH-].[Na+].C1COCC1>O>[N:11]1([C:8]2[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 45790075Methyl 5-(piperidin-1-yl)pyrazine-2-carboxylate

Product 1

HCID 457897585-(Piperidin-1-yl)pyrazine-2-carboxylic acidYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester (Preparation 42, 85.1 g, 384 mmol) was added to a solution of sodium hydroxide (61.5 g, 1.53 mol) in water (760 mL). The mixture was stirred mechanically for 1 hour at room temperature. THF (300 mL) was added and stirring was continued for 3 hours. The volatile solvents were removed in vacuo and the remaining aqueous solution was adjusted to pH 4. The mixture was cooled on ice to induce precipitation of the product. The resulting solid was collected by filtration and dried in vacuo to give the title compound as a white solid (56 g) in a 70% yield.

Workup

  1. stirringstirring
  2. waitwas continued for 3 hours
  3. customThe volatile solvents were removed in vacuo
  4. temperatureThe mixture was cooled on ice
  5. customprecipitation of the product
  6. filtrationThe resulting solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-eb18ca5f28ba46488bf0e9bffbbbb742
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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