6-Chloro-8-aminoquinoline → 6-Chloro-8-(piperazin-1-yl)quinoline

HRID 2241993Notes

Reaction equation

HRID 2241993 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:12])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Cl.Cl[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl>ClC1C=CC=CC=1.O>[Cl:12][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([N:1]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 796186-Chloro-8-aminoquinolineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 592048546-Chloro-8-(piperazin-1-yl)quinolineYield 29.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
135 °C

Procedure

8-amino-6-chloroquinoline (Step 1, 0.49 g) and bis(chloroethyl)amine hydrochloride (0.49 g) were dissolved in chlorobenzene (13 mL) and heated with vigorous stirring at 135° C. for 5 days. The reaction was cooled to room temperature, diluted with water and extracted with Et2O. The aqueous phase was made basic by addition of solid Na2CO3 and then extracted with Et2O. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator to give the desired compound (0.20 g) as a yellow semi-solid; MS (ES) m/z (relative intensity) 248 (M+H)+ (100).

Workup

  1. temperatureheated
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with Et2O
  4. additionThe aqueous phase was made basic by addition of solid Na2CO3
  5. extractionextracted with Et2O
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-019b4a153ef24b70b452c13640987226
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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