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

HRID 2241984노트

반응식

HRID 2241984 반응식
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[C:20]([F:21])=[C:19]4[C:14]([CH:15]=[CH:16][CH:17]=[N:18]4)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>O1CCCC1>[F:21][C:20]1[C:11]([N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 592048707-(1.4-Dioxa-8-azaspiro[4.5]dec-8-yl)-8-fluoroquinoline

생성물 1

HCID 592048601-(8-Fluoroquinolin-7-yl)piperidin-4-one수율 80.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 7-(1.4-dioxa-8-azaspiro[4.5]dec-8-yl)-8-fluoroquinoline (Example J, Step 2; 1.30 g) in tetrahydrofuran (60 mL) was added aq. 2N aqueous HCl (10 mL). The resulting mixture was stirred at room temperature for 18 hours and then heated at 60° C. for 5 hours. The reaction mixture was cooled to room temperature, poured into 1N 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 using hexane/acetone to give 0.89 g of the desired product as a yellow solid; MS (ES) m/z (relative intensity): 245 (M+H)+ (100).

후처리

  1. temperatureheated at 60° C. for 5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-7480e53ad55441b9859bfbb6fbfbaac9
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671056B2

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