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Hydrochloric Acid → 2,3-Dihydro-1'-[3-(4-fluorobenzoyl)propyl]-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride

HRID 261477
ノート
印刷プレビュー

反応式

HRID 261477 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:16][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][C:8]=2[CH:17]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C1O[C:29]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)([CH2:30][CH2:31][CH2:32][Cl:33])[O:28]C1.Cl.[OH-].[Na+]>C(O)CCC.CO>[ClH:33].[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:29]([CH2:30][CH2:31][CH2:32][N:13]2[CH2:12][CH2:11][C:10]3([CH2:9][C:8]4[CH:17]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=4[O:16]3)[CH2:15][CH2:14]2)=[O:28])=[CH:39][CH:38]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 127332362,3-Dihydro-5-nitrospiro[benzofuran-2,4'-piperidine]

生成物 1

HCID 20394317
2,3-Dihydro-1'-[3-(4-fluorobenzoyl)propyl]-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 887Methanol溶媒

実験手順

A stirred suspension of 5.2 g of 2,3-dihydro-5-nitrospiro[benzofuran-2,4'-piperidine] free base of C, 7.0 g of potassium carbonate, a few grains of potassium iodide and 6.2 g of γ-chloro-p-fluorobutyrophenone ethylene ketal in 200 ml of n-butyl alcohol is refluxed for 24 hours. Thereafter, the reaction mixture is permitted to cool to ambient temperature and then filtered. The filtrate is evaporated to dryness, leaving a brown oil. The oil is dissolved in 200 ml of methyl alcohol and 100 ml of 3N hydrochloric acid and this solution is stirred at ambient temperature for 18 hours and then basified with 6 N sodium hydroxide. The alkaline mixture is extracted with ethyl acetate and the ethyl acetate extracts are successively dried and evaporated to dryness, leaving an oil. The oil is chromatographed on a silica gel column eluting with chloroform which leads to a solid. The solid is dissolved in ether where it is converted to its hydrochloric acid salt, a white precipitate. The precipitate is recrystallized twice from ethyl alcohol to give the product 2,3-dihydro-1'-[3-(4-fluorobenzoyl)propyl]-5-nitrospiro[benzofuran-2,4'-piperidine]hydrochloride, mp 245°-247° C.

後処理

  1. filtrationfiltered
  2. customThe filtrate is evaporated to dryness
  3. customleaving a brown oil
  4. extractionThe alkaline mixture is extracted with ethyl acetate
  5. dry with materialthe ethyl acetate extracts are successively dried
  6. customevaporated to dryness
  7. customleaving an oil
  8. customThe oil is chromatographed on a silica gel column
  9. washeluting with chloroform which
  10. dissolutionThe solid is dissolved in ether where it
  11. customThe precipitate is recrystallized twice from ethyl alcohol

出典と根拠

ORDレコード
ord-ce11ef7c553840ae9c20a303cba8dce1
出典データセット
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04166120

反応ノート

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