Chloroform → 9-Phenyl-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356173

Reaktionsgleichung

Reaktionsgleichung von HRID 356173
[C:1]1(=[O:29])[N:5]([CH2:6][C:7]([N:9]2[CH:15]3[CH2:16][CH2:17][CH2:18][CH:14]3[C:13](=[O:19])[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>BrC1C=CC=CC=1.[Cu]I>[C:2]1([N:12]2[C:13](=[O:19])[CH:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[N:9]([C:7](=[O:8])[CH2:6][N:5]3[C:4](=[O:24])[C:3]4=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]4[C:1]3=[O:29])[C:10]3[CH:23]=[CH:22][CH:21]=[CH:20][C:11]2=3)[CH:3]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

6

Edukt 3

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 189405414-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Produkt 1

HCID 189406169-Phenyl-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneAusbeute 126 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 7961BromobenzeneLösungsmittel

Versuchsvorschrift

To a suspension of 4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (584 mg, 1.5 mmol) and potassium carbonate (228 mg, 1.6 mmol) in bromobenzene (3 mL) was added copper (I) iodide (57 mg, 0.3 mmol), and the mixture was heated for 90 minutes under reflux. To the reaction mixture was added chloroform, which was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was recrystallized from chloroform-ethanol-hexane to give 440 mg (yield 63%) of a mixture of cis-compound and trans-compound (3:2), m.p. 272°-273° C.

Aufarbeitung

  1. temperaturethe mixture was heated for 90 minutes
  2. temperatureunder reflux
  3. filtrationwas subjected to filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe concentrate was recrystallized from chloroform-ethanol-hexane

Quellen und Nachweise

ORD-Eintrag
ord-497a574e32204599bf338740bc3a80f7
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834463

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