Benzylamine → 4-(3-Benzylamino-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](F)[C:15]=2[N+:21]([O-:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:31][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:15]=2[N+:21]([O-:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
4-(3-Fluoro-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.300 g, 0.923 mmol) and benzylamine (0.110 mL, 1.015 mmol) were combined in 1 mL dimethylsulfoxide with potassium carbonate (0.318 g, 2.308 mmol), and the reaction mixture was heated to 120° C. for 2 hours. The reaction mixture was poured onto 100 g icewater and extracted twice with 100 mL ethyl acetate. The combined organic phases were washed twice with 50 mL water, once with 50 mL brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by flash chromatography (1% to 15% ethyl acetate in hexanes) to afford 0.208 g (0.50 mmol, 54%) of 4-(3-benzylamino-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester. MS: 413 (M+H)+.
Workup
- additionThe reaction mixture was poured onto 100 g icewater
- extractionextracted twice with 100 mL ethyl acetate
- washThe combined organic phases were washed twice with 50 mL water, once with 50 mL brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue is purified by flash chromatography (1% to 15% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-0d6afa7cf7e64f3896f9b4bcc1abccfd
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582760B2
Reaction notes
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