Triethylamine → 7-Chloro-4-[4-(2-chlorobenzylaminocarbonyl)piperazin-1-yl]quinoline

HRID 1353372

Reaction equation

HRID 1353372 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].Cl[C:11](OC1C=CC([N+]([O-])=O)=CC=1)=[O:12].C(N(CC)CC)C.[Cl:30][C:31]1[CH:40]=[C:39]2[C:34]([C:35]([N:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1>CCCCCC.CCOC(C)=O>[Cl:30][C:31]1[CH:40]=[C:39]2[C:34]([C:35]([N:41]3[CH2:46][CH2:45][N:44]([C:11]([NH:5][CH2:4][C:3]4[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=4[Cl:1])=[O:12])[CH2:43][CH2:42]3)=[CH:36][CH:37]=[N:38]2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 666482-ChlorobenzylamineHCID 821294-Nitrophenyl chloroformateHCID 7383897-Chloro-4-(piperazin-1-yl)quinoline

Product 1

HCID 211017567-Chloro-4-[4-(2-chlorobenzylaminocarbonyl)piperazin-1-yl]quinoline

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2-Chlorobenzylamine (60 μL, 0.5 mmol), 4-nitrophenyl chloroformate (101 mg, 0.5 mmol), triethylamine (238 μL, 1.7 mmol), and 7-chloro-4-(piperazin-1-yl)quinoline (124 mg, 0.5 mmol) are treated according to method D delivering 147 mg of the product as a pale yellow solid after column chromatography with hexane-EtOAc.

Sources & evidence

ORD record
ord-6fda6e1b6d514a21b20a25cdcb19dbe5
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Linked notes

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