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

HRID 1929935
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HRID 1929935 반응식
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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3fb98b11aea44cfc8fad05840d20b737
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08188093B2

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