Piperidine → Methyl 5-(piperidin-1-yl)pyrazine-2-carboxylate

HRID 340089Notes

Reaction equation

HRID 340089 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](Cl)=[CH:7][N:6]=1)=[O:4].CCN(C(C)C)C(C)C.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 45790075Methyl 5-(piperidin-1-yl)pyrazine-2-carboxylateYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-pyrazine-2-carboxylic acid methyl ester (Preparation 41, 85 g, 492 mmol) in DMF (365 mL) was added DIPEA (129 mL, 738 mmol) and piperidine (58.4 mL, 591 mmol) and the resulting solution was stirred at room temperature for 18 hours. The reaction mixture was poured onto water (4 L) and the resulting precipitate was collected by filtration to give the title compound as a white solid (85.12 g) in a 78% yield.

Workup

  1. additionThe reaction mixture was poured onto water (4 L)
  2. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-6d52f244343a415580e24e8ccf05653b
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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