Hydrochloric Acid → 6-(4-Fluoro-phenyl)-5-piperidin-1-yl-pyrazine-2-carboxylic acid

HRID 1929935Notes

Reaction equation

HRID 1929935 reaction equation
O1CCCC1.C[O:7][C:8]([C:10]1[CH:15]=[N:14][C:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[N:11]=1)=[O:9].[OH-].[Li+].Cl>O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:12]2[N:11]=[C:10]([C:8]([OH:9])=[O:7])[CH:15]=[N:14][C:13]=2[N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 675048406-(4-Fluoro-phenyl)-5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 675049236-(4-Fluoro-phenyl)-5-piperidin-1-yl-pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (5 ml) solution of 6-(4-Fluoro-phenyl)-5-piperidin-1-yl-pyrazine-2-carboxylic acid methyl ester (0.48 g, 1.52 mmol, 1.0 eq) was added a solution of lithium hydroxide (1M, 1.52 ml, 1.52 mmol, 1.0 eq) in water. The mixture was stirred overnight at room temperature after which time the resulting solution was acidified with hydrochloric acid (pH˜5) and aqueous phase extracted with ethyl acetate (2×10 ml). The organic phase was dried over magnesium sulfate and concentrated in vacuo to afford 6-(4-fluoro-phenyl)-5-piperidin-1-yl-pyrazine-2-carboxylic acid as white crystals. Yield=0.42 g (91%). 1H NMR (400 MHz, DMSO): δ 1.46-1.53 (6H, m), 3.22-3.25 (4H, m), 7.32 (2H, t, J=8.87 Hz), 7.82-7.86 (2H, m), 8.62 (1H, s).

Workup

  1. extractionextracted with ethyl acetate (2×10 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fb98b11aea44cfc8fad05840d20b737
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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