Triethylamine → 4-(4-Methyl-3-nitro-benzyl)-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.C(N(CC)CC)C.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(OCC)(=O)C.O>CN(C=O)C>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 78 °C
Procedure
To a solution of 4-chloromethyl-1-methyl-2-nitro-benzene (2 g) and triethylamine (3 ml) in DMF (10 ml) was added piperazine-1-carboxylic acid tert-butyl ester (2.01 g) and the stirred reaction heated at 78° C. for 15 hr. After cooling to room temperature, the reaction was poured into ethyl acetate/water and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water, aqueous KHSO4, aqueous K2CO3 and brine, dried (Na2SO4) and concentrated to leave the sub-title compound as a brown oil (3.5 g).
Workup
- customthe stirred reaction
- temperatureAfter cooling to room temperature
- customthe organic layer was separated
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe combined organic extracts were washed with water, aqueous KHSO4, aqueous K2CO3 and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9e439aa324f840f4b0270f98344d9abe
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555541B1
Reaction notes
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