Diisopropylethylamine → methyl 4-(4-nitro-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate
Reaction equation
Cl[CH:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl.[CH3:24][O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27]>C(#N)C.CCOC(C)=O>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH:2]2[N:31]1[CH2:32][CH2:33][N:28]([C:26]([O:25][CH3:24])=[O:27])[CH2:29][CH2:30]1)([O-:13])=[O:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 79 °C
Procedure
To a room temperature solution of 1-Chloro-4-nitro-2,3-dihydro-1H-indene (221 mg, 1.12 mmol, 1.0 equiv) and DIPEA (430 μL, 2.46 mmol, 2.2 equiv) in dry acetonitrile (1.6 mL) was added methylpiperazine carboxylate hydrochloride salt (444 mg, 2.46 mmol, 2.2 equiv) as a solid in one portion. The resulting reaction mixture was heated to 79° C. overnight. The reaction mixture was allowed to cool to RT and diluted with EtOAc. The organic layer was extracted with 1 M HCl (3×20 mL), and the combined aqueous layers were treated with 3 N NaOH until the pH=10. The resulting solution was extracted three times with EtOAc, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a brown oil (239 mg, 78%). LCMS [M+H]+=306.1.
Workup
- customThe resulting reaction mixture
- temperatureto cool to RT
- extractionThe organic layer was extracted with 1 M HCl (3×20 mL)
- additionthe combined aqueous layers were treated with 3 N NaOH until the pH=10
- extractionThe resulting solution was extracted three times with EtOAc
- dry with materialthe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f6111a8b74104884ac40d923feb071c7
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653081B2
Reaction notes
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