Hydrochloric Acid → 1-(7-Fluoroquinolin-8-YL)piperidin-4-one

HRID 2241982ノート

反応式

HRID 2241982 の反応式
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[C:12]([F:21])=[CH:13][CH:14]=[C:15]4[C:20]=3[N:19]=[CH:18][CH:17]=[CH:16]4)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>O1CCCC1>[F:21][C:12]1[C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[C:20]2[C:15]([CH:16]=[CH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 592048418-(1.4-Dioxa-8-azaspiro[4.5]dec-8-yl)-7-fluoroquinoline

生成物 1

HCID 573365271-(7-Fluoroquinolin-8-YL)piperidin-4-one収率 79.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of 8-(1.4-dioxa-8-azaspiro[4.5]dec-8-yl)-7-fluoroquinoline (Step 2, 1.73 g) in tetrahydrofuran (50 mL) was added aq. 2N aqueous HCl (10 mL). The resulting mixture was stirred at 50° C. for 3 hours. The reaction mixture was then cooled to room temperature, poured into 2.5 N aqueous NaOH and extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give 1.17 g of the desired product as a yellow oil; MS (ES) m/z (relative intensity): 245 (M+H)+ (100).

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe crude product was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-dc5fc1d201e44452877f359bbf661964
出典データセット
uspto-grants-2010_03
特許番号
US07671056B2

反応ノート

読み込み中…