Hydrochloric Acid → (2-Fluorophenyl)(1-methylpiperidin-4-yl)methanone--hydrogen chloride (1/1)

HRID 986105노트

반응식

HRID 986105 반응식
[Mg].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([Cl:9])[CH2:5][CH2:4]1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#N.[Cl-].[NH4+].Cl.[O:22]1CCCC1>C(Br)C.CCOCC>[ClH:9].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]([CH:6]1[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]1)=[O:22]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran3회HCID 25517Ammonium ChlorideHCID 678552-FluorobenzonitrileHCID 793424-chloro-N-methylpiperidineHCID 5462224Magnesium

생성물 1

HCID 13180318(2-Fluorophenyl)(1-methylpiperidin-4-yl)methanone--hydrogen chloride (1/1)수율 42%

시약·촉매·용매 2

HCID 6332Ethyl Bromide촉매HCID 3283Diethyl Ether용매

실험 절차

To a suspension of 7.6 g of magnesium turnings in 25 ml of tetrahydrofuran was added a few drops of ethyl bromide, with stirring under nitrogen. After the reaction began approximately 50.0 g of N-methyl-4-chloropiperidine in 125 ml of tetrahydrofuran was added dropwise at a rate such that moderate reflux was maintained. The reaction was heated under reflux for an additional hour. A solution of 37.2 g of o-fluorobenzonitrile in 30 ml of tetrahydrofuran was added dropwise. After completion of the addition the reaction mixture was heated under reflux for two hrs and stirred overnight at room temperature. The reaction mixture was poured into a solution of 85 g of ammonium chloride in 1200 ml of ice water and heated on a stream bath for 3 hrs. The mixture was cooled, extracted with benzene (3x, 250 ml) and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave an oil. A 1.0 g-portion of the oil was dissolved in ether and a solution of ethereal hydrogen chloride was added. The precipitate was collected, dried and twice recrystallized from ethanol-ether to give 0.5 g (42%) of product, mp 167°-169° C.

후처리

  1. additionwas added dropwise at a rate such
  2. temperaturethat moderate reflux
  3. temperaturewas maintained
  4. temperatureThe reaction was heated
  5. temperatureunder reflux for an additional hour
  6. additionAfter completion of the addition the reaction mixture
  7. temperaturewas heated
  8. temperatureunder reflux for two hrs
  9. stirringstirred overnight at room temperature
  10. temperatureheated on a stream bath for 3 hrs
  11. temperatureThe mixture was cooled
  12. extractionextracted with benzene (3x, 250 ml)
  13. dry with materialdried over anhydrous sodium sulfate
  14. customRemoval of the solvent under reduced pressure
  15. customgave an oil
  16. customThe precipitate was collected
  17. customdried
  18. customtwice recrystallized from ethanol-ether

출처 및 근거

ORD 기록
ord-507d00b9409f4d90b0acd8bad22c9482
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04710573

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