Reaktion #82151

ord-93a7c98bbcbc472580c091492ec5d4fa

Reaktionsgleichung

CC1(c2ccccc2CC(=O)N=[N+]=[N-])CC2OCCOC2CC1=O
acyl azide
CC1(c2ccccc2CC(=O)N=[N+]=[N-])CC2OCCOC2CC1=O
2-(4'-ethylenedioxy-1'-methyl-2'-oxocyclohexyl)-phenylacetyl azide
CN(C)C=O
dimethylformamide
CC(=O)O
acetic acid
→
CC1(c2ccccc2CN)CCC(=O)CC1=O
2-(2', 4'-dioxo-1'-methyl-cyclohexyl)-benzyl amine

Edukte

CC1(c2ccccc2CC(=O)N=[N+]=[N-])CC2OCCOC2CC1=O
acyl azide
CC1(c2ccccc2CC(=O)N=[N+]=[N-])CC2OCCOC2CC1=O
2-(4'-ethylenedioxy-1'-methyl-2'-oxocyclohexyl)-phenylacetyl azide
CN(C)C=O
dimethylformamide
CC(=O)O
acetic acid

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe solution is cooled

Vorschrift

The acyl azide 5 is dissolved in dimethylformamide and heated to 100° C. until nitrogen evolution ceases. The solution is cooled and treated with aqueous acetic acid to form 2-(2', 4'-dioxo-1'-methyl-cyclohexyl)-benzyl amine 6. Diethyl ether is added and the solution is washed successively with saturated sodium bicarbonate solution, water, and saturated salt solution and dried over anhydrous sodium sulfate. The solvent is removed by rotoevaporation to yield 1,2,3,4,4a,5,6,10b-octahydro- 10b-methyl-3-phenanthridinone 7.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05621104uspto-grants-1997_04