4,7-Dichloroquinoline → 7-Chloro-4-(2,5-diazanorborn-2-yl)quinoline

HRID 1353358Notes

Reaction equation

HRID 1353358 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.Br.Br.[CH:15]12[CH2:21][CH:18]([NH:19][CH2:20]1)[CH2:17][NH:16]2.C1N2CCN(CC2)C1.C(Cl)Cl.CO>C(O)CCC>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:16]3[CH2:17][CH:18]4[CH2:21][CH:15]3[CH2:20][NH:19]4)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 68664,7-DichloroquinolineHCID 9237DabcoHCID 162131472,5-Diazabicyclo[2.2.1]heptane dihydrobromideHCID 21226129Dichloromethane methanol

Product 1

HCID 211019597-Chloro-4-(2,5-diazanorborn-2-yl)quinoline

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4,7-Dichloroquinoline (0.38 g, 1.9 mmol) and 2,5-diazanorbornane dihydrobromide (1.0 g, 3.8 mmol), and DABCO (1.3 g, 11.4 mmol) in n-butanol (20 mL) are reacted according to method B yielding the product after column chromatography with CH2Cl2-MeOH.

Sources & evidence

ORD record
ord-db71e1ba5cca4d6fb728f947868bd64e
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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