4-Nitrobenzyl chloroformate → 1-[4-(N-4-nitrobenzyloxycarbonylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine
Reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[N+:34]([C:37]1[CH:47]=[CH:46][C:40]([CH2:41][O:42][C:43](Cl)=[O:44])=[CH:39][CH:38]=1)([O-:36])=[O:35]>O1CCCC1>[N+:34]([C:37]1[CH:38]=[CH:39][C:40]([CH2:41][O:42][C:43]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)[CH2:10][CH2:9]3)=[O:7])=[CH:23][CH:24]=2)=[O:44])=[CH:46][CH:47]=1)([O-:36])=[O:35]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1 g of 1-[4-aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine and 0.4 g of Hunig base (=N-ethyldiisopropylamine) are dissolved in 15 ml of tetrahydrofuran. A solution of 0.75 g of chloroformic acid 4-nitrobenzyl ester in 5 ml of tetrahydrofuran is added dropwise thereto. The reaction solution is stirred for 3.5 hours at room temperature and for 2 hours at a bath temperature of 55°. The solution is concentrated by evaporation and the residue is taken up in methylene chloride and washed with water. Colourless crystals of 1-[4-(N-4-nitrobenzyloxycarbonylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine having a melting point of 146°-148° are obtained from alcohol.
Workup
- concentrationThe solution is concentrated by evaporation
- washwashed with water
Sources & evidence
- ORD record
- ord-0446c28d2be64a35af886c1a6a40c558
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05321027
Reaction notes
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