Ammonium Hydroxide → 4,4-Dimethylpiperidine-2,6-dione

HRID 1109148

Reaktionsgleichung

Reaktionsgleichung von HRID 1109148
Cl.COC1C2CC[C@H]3[C@H](CCN3CCCC[N:21]3[C:26](=[O:27])[CH2:25][C:24]([CH3:29])([CH3:28])[CH2:23][C:22]3=[O:30])C=2C=CC=1.Cl.N1C=CC=CC=1.[OH-].[NH4+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][C:24]1([CH3:29])[CH2:25][C:26](=[O:27])[NH:21][C:22](=[O:30])[CH2:23]1

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 131718487rac-cis-1-[4-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)-butyl]-4,4-dimethyl-piperidine-2,6-dione hydrochloride

Produkt 1

HCID 142924,4-Dimethylpiperidine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

8.8 g (22.1 mmol) of rac-cis-1-[4-(6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)-butyl]-4,4-dimethyl-piperidine-2,6-dione hydrochloride were mixed well with 100 g of pyridine hydrochloride and stirred under an argon atmosphere in an oil bath for 4 hours at an oil bath temperature of 180°. After cooling the mixture was treated with ice-water, whereupon the brown solution was made alkaline with ammonium hydroxide solution and then extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulphate and evaporated. The brown oily product obtained (9.8 g) was chromatographed on a 30-fold amount of silica gel. The uniform eluates obtained in a thin-layer chromatogram using methylene chloride/ethyl acetate 1:1 were pooled and evaporated. The oil obtained crystallized after treatment with hexane. There were obtained 5.5 g (65%) of rac-cis-1-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)-butyl]-4,4-dimethyl-piperidine-2,6-dione in the form of yellowish crystals of m.p. 131°-132°.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe brown oily product obtained (9.8 g)
  7. customwas chromatographed on a 30-fold amount of silica gel
  8. customThe uniform eluates obtained in a thin-layer chromatogram
  9. customevaporated
  10. customThe oil obtained
  11. customcrystallized after treatment with hexane

Quellen und Nachweise

ORD-Eintrag
ord-c0c5e1e4c5d441dd9f2075f3a8122e2b
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05318966

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