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

HRID 881028ノート

反応式

HRID 881028 の反応式
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]

参加物

7

反応物 4

HCID 6569Methyl Ethyl Ketone2 回HCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 18409081tert-Butyl 4-(3-bromopropyl)piperidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eafa19f91cf043eda6de1d2bfb89bf42
出典データセット
uspto-grants-2015_03
特許番号
US08993603B2

反応ノート

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