Methyl Ethyl Ketone → Tert-butyl 4-[3-(4-cyano-3-fluorophenoxy)propyl]-1-piperidinecarboxylate

HRID 881028노트

반응식

HRID 881028 반응식
CC(=O)CC.Br[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[F:23][C:24]1[CH:31]=[C:30]([OH:32])[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[C:26]([C:25]1[CH:28]=[CH:29][C:30]([O:32][CH2:7][CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:31][C:24]=1[F:23])#[N:27]

참가 물질

7

반응물 4

HCID 6569Methyl Ethyl Ketone2회HCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 18409081tert-Butyl 4-(3-bromopropyl)piperidine-1-carboxylate

생성물 1

HCID 59263029Tert-butyl 4-[3-(4-cyano-3-fluorophenoxy)propyl]-1-piperidinecarboxylate수율 54.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A 2-butanone (7.6 mL) solution of 1.12 g of tert-butyl 4-(3-bromopropyl)-1-piperidinecarboxylate was added to a 2-butanone (7.0 mL) mixture of 0.50 g of 2-fluoro-4-hydroxybenzonitrile and 0.56 g of potassium carbonate, which was then heated to reflux for 6 hours and 30 minutes. After cooling down to room temperature, the reaction mixture was added to a mixture of ethyl acetate and water. The organic layer was separated, washed with water, and dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to provide 0.72 g of tert-butyl 4-[3-(4-cyano-3-fluorophenoxy)propyl]-1-piperidinecarboxylate as colorless oily form.

후처리

  1. temperaturewas then heated
  2. temperatureto reflux for 6 hours and 30 minutes
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resultant residue was purified

출처 및 근거

ORD 기록
ord-eafa19f91cf043eda6de1d2bfb89bf42
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993603B2

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