Trifluoroacetic acid → 6-Chloro-4-(piperazin-1-yl)quinoline

HRID 1353310Notes

Reaction equation

HRID 1353310 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(OC([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9360754,6-Dichloroquinoline

Product 1

HCID 114706516-Chloro-4-(piperazin-1-yl)quinolineYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,6-Dichloroquinoline (De, D., Byers L. D., Krogstad, D. J. J. Heterocyclic Chem. 1997, 34, 315) (0.34 g, 1.7 mmol) and 1-tert-butoxycarbonylpiperazine (1.58 g, 8.5 mmol) are reacted according to method A. The Boc group is cleaved with trifluoroacetic acid (5 mL) in CH2Cl2 (5 mL) giving 0.25 g of the product.

Sources & evidence

ORD record
ord-0553ac122dcd4c0d88ae55d564a70842
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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