Pyridine → HCID 86751948, compound
Reaction equation
[CH3:1][C@@H:2]([NH:13][CH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.Cl.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1.N1C=CC=CC=1>C(O)C>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][N:30]=[C:17]2[CH2:18][CH2:19][CH:14]([NH:13][C@H:2]([CH3:1])[CH2:3][C:4]3[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=3)[CH2:15][CH2:16]2)=[CH:25][CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 22.3 gm (85.01 mMol) N-((R)-(+)-a-methyl-(4-nitrophenyl)ethyl)-4-aminocyclohexanone in 375 mL ethanol were added 19.0 gm (85.0 mMol) 4-bromophenylhydrazine hydrochloride and 6.73 gm (85.1 mMol) pyridine. The reaction mixture was heated to 80° C. for 48 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in dichloromethane and the organic solution was washed sequentially with aqueous potassium carbonate and saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure to give 31.66 gm (86%) N-((R)-(+)-a-methyl-(4-nitrophenyl)ethyl)-4-aminocyclohexanone 4-bromophenylhydrazone as a brown solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in dichloromethane
- washthe organic solution was washed sequentially with aqueous potassium carbonate and saturated aqueous sodium chloride
- dry with materialThe remaining organics were dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d6c8fc665a9848c5b7d48dc1ff6d936b
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05708187
Reaction notes
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