Water → 2,3-Dihydro-1'-cyclopropylcarbonylspiro[benzofuran-2,4'-piperidine]

HRID 261497ノート

反応式

HRID 261497 の反応式
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH:7]1[CH2:12][CH2:11][C:10]2([CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13]2)[CH2:9][CH2:8]1.O.[OH-].[Na+]>N1C=CC=CC=1>[CH:1]1([C:4]([N:7]2[CH2:12][CH2:11][C:10]3([CH2:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[O:13]3)[CH2:9][CH2:8]2)=[O:5])[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 127332303H-Spiro(1-benzofuran-2,4'-piperidine)

生成物 1

HCID 203942582,3-Dihydro-1'-cyclopropylcarbonylspiro[benzofuran-2,4'-piperidine]

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

1.8 g of cyclopropylcarbonyl chloride are added dropwise to a stirred solution at 0° C. of 3.2 g of 2,3-dihydrospiro[benzofuran-2,4'-piperidine] in 50 ml of pyridine. After total addition the reaction is stirred for 60 hours at ambient temperature and then heated at reflux for 3 hours. Thereafter, the reaction mixture is successively permitted to cool to ambient temperature, poured into 500 ml of water, basified with 20% sodium hydroxide and the solvent is removed under reduced pressure. The residue is triturated with 500 ml of water, extracted twice with ethyl acetate and the combined extracts are dried and the solvent is removed under reduced pressure, leaving a solid. The solid is recrystallized thrice from water to provide white flakes, 2,3-dihydro-1'-cyclopropylcarbonylspiro[benzofuran-2,4'-piperidine], mp 111°-113° C.

後処理

  1. additionAfter total addition the reaction
  2. temperatureheated
  3. temperatureat reflux for 3 hours
  4. temperatureto cool to ambient temperature
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is triturated with 500 ml of water
  7. extractionextracted twice with ethyl acetate
  8. customthe combined extracts are dried
  9. customthe solvent is removed under reduced pressure
  10. customleaving a solid
  11. customThe solid is recrystallized thrice from water

出典と根拠

ORDレコード
ord-ea94c57c3b624e278473202240485871
出典データセット
uspto-grants-1979_08
特許番号
US04166119

反応ノート

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