Cyclohexene → HCID 18183148, compound

HRID 430663Notes

Reaction equation

[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[C:10]3[CH:16]=[C:15]4[O:17][CH2:18][O:19][C:14]4=[CH:13][C:11]=3[CH2:12][C:6]2=[N:5][C:4]=1[CH3:29])[CH3:2].C1CCCCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:9]2[C:10]3[CH:16]=[C:15]4[O:17][CH2:18][O:19][C:14]4=[CH:13][C:11]=3[CH2:12][C:6]3=[N:5][C:4]([CH3:29])=[C:3]([CH2:1][CH3:2])[N:7]3[N:8]=2)=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 110 °C

Procedure

527 mg of 8-ethyl-9-methyl-5-(4-nitrophenyl)-11H-1,3-dioxolo[4,5-h)imidazo[1,2-c][2,3]benzodiazepine is mixed in 11 ml of ethanol with 5.4 ml of cyclohexene and 106 mg of palladium hydroxide on carbon (Pearlman's catalyst), and it is stirred for 3 hours at a bath temperature of 110° C. After catalyst is filtered out, it is concentrated by evaporation, and the residue is chromatographed on silica gel with ethyl acetate as an eluant. After combining the corresponding fractions and recrystallization from ethanol, 348 mg of 5-(4-aminophenyl)-8-ethyl-9-methyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine with a melting point of 227-228° C. is obtained.

Workup

filtrationAfter catalyst is filtered out
concentrationit is concentrated by evaporation
customthe residue is chromatographed on silica gel with ethyl acetate as an eluant
customthe corresponding fractions and recrystallization from ethanol, 348 mg of 5-(4-aminophenyl)-8-ethyl-9-methyl-11H-1,3-dioxolo[4,5-h]imidazo[1,2-c][2,3]benzodiazepine with a melting point of 227-228° C.
customis obtained

Sources & evidence

ORD record: ord-a5be3787b35547b7b6c99c3e68123004
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323197B1

Reaction notes

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