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

HRID 261477
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 261477
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 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]

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ce11ef7c553840ae9c20a303cba8dce1
Quelldatensatz
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04166120

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