Sodium Hydroxide → 1-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 1903263노트

반응식

HRID 1903263 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]12[C:17](=O)[NH:16][C:15](=O)[CH:14]1[CH2:13]2.COCCO[AlH2-]OCCOC.[Na+].[H-].[OH-].[Na+]>CCOCC.C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]12[CH2:13][CH:14]1[CH2:15][NH:16][CH2:17]2

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 16684438Red-AlHCID 867362351-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)cyclopropanedicarboximide

생성물 1

HCID 867362331-(p-Chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride

시약·촉매·용매 2

HCID 241Benzene용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 0.28 g. of 1-(p-chloro-α,α,α-trifluoro-m-tolyl)cyclopropanedicarboximide in 10 ml. of benzene is added one ml. of Vitride®. This is refluxed for one hour, cooled to ambient temperature, and the excess hydride reagent is decomposed with one ml. of 10 N sodium hydroxide. The benzene layer is washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give an amber-colored oil. This is dissolved in ether and dry hydrogen chloride is bubbled into the solution. The resultant precipitate is collected by filtration and recrystallized from isopropyl alcohol to give 1-(p-chloro-α,α,α-trifluoro-m-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride. Purification of the hydrochloride by recrystallization from acetonitrile gives colorless crystals, m.p. 164°-166° C.

후처리

  1. temperatureThis is refluxed for one hour
  2. washThe benzene layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto give an amber-colored oil
  6. customdry hydrogen chloride is bubbled into the solution
  7. filtrationThe resultant precipitate is collected by filtration
  8. customrecrystallized from isopropyl alcohol

출처 및 근거

ORD 기록
ord-3c37bae69f0348d08f017e82949161ec
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04435419

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