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Thionyl Chloride → 8-{3-[4-(2-Isopropoxy-phenyl)-piperazin-1-ylmethyl]-benzyl}-8-aza-spiro[4.5]decane-7,9-dione

HRID 1034142
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Reaktionsgleichung

Reaktionsgleichung von HRID 1034142
[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[CH2:21][NH2:22])[CH2:13][CH2:12]1)[CH3:3].[CH2:26]1[CH2:30][C:29]2([CH2:37][C:35](=O)[O:34][C:32](=[O:33])[CH2:31]2)[CH2:28][CH2:27]1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:3][CH:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH2:21][N:22]3[C:35](=[O:34])[CH2:37][C:29]4([CH2:30][CH2:26][CH2:27][CH2:28]4)[CH2:31][C:32]3=[O:33])[CH:23]=[CH:24][CH:25]=2)[CH2:13][CH2:12]1)[CH3:1]
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Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 79743Cyclopentane-1,1-diacetic anhydrideHCID 10521066HCID 10521066, Verbindung

Produkt 1

HCID 107198468-{3-[4-(2-Isopropoxy-phenyl)-piperazin-1-ylmethyl]-benzyl}-8-aza-spiro[4.5]decane-7,9-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 3-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]-benzyl amine (2.50 g, 7.37 mmol), prepared as described above, 3,3-tetramethyleneglutaric anhydride (1.12 g, 6.66 mmol), and toluene (30 mL) was heated to reflux, cooled slightly, and treated with thionyl chloride (9.72 mL, 13.32 mmol). The resulting slurry was refluxed for 30 min, cooled and the solid collected by filtration. This material was partitioned between CH2Cl2 /3N NAOH and the organic layer was separated, dried, filtered and evaporated giving 8-[[3-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]phenyl]methyl]-8-azaspiro[4.5]decane-7,9-dione as a crude oil. The oil was converted to the maleate salt in i-PrOH. The isolated residue was converted back to the free base which was obtained as an oil (2.10 g). Chromatography of this material on flash silica using EtOAc/hexane of varying proportions gave an oil which was dissolved in ether and added to ethereal HCl causing formation of a solid. Filtration afforded 8-[[3-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]phenyl]methyl]-8-azaspiro[4.5]decane-7,9-dione dihydrochloride (0.94 g, 25%), m.p. 212°-216° C. (dec). 1H NMR and mass spectral analysis supported the assigned structure.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturecooled slightly
  4. temperatureThe resulting slurry was refluxed for 30 min
  5. temperaturecooled
  6. filtrationthe solid collected by filtration
  7. customThis material was partitioned between CH2Cl2 /3N NAOH
  8. customthe organic layer was separated
  9. customdried
  10. filtrationfiltered
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2597969e49ec44b5ab00fc40925b6fd7
Quelldatensatz
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05314885

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