Hydrochloric Acid → 2-Methyl-5-piperazin-1-yl-quinoline

HRID 15821

Reaction equation

HRID 15821 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[N:3]=1.Cl>CC(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49851900Tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate

Product 1

HCID 498519012-Methyl-5-piperazin-1-yl-quinolineYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,1-dimethylethyl 4-(2-methyl-5-quinolinyl)-1-piperazinecarboxylate in 2-propanol (3 vol) was added dropwise hydrochloric acid (37%, 3 vol). The mixture was stirred at 40° C. for 1.5 hours then concentrated. Water (30 vol) was added and the solution was extracted with ethyl acetate (3×20 vol). The aqueous layer was basified with an aqueous sodium carbonate solution then extracted with dichloromethane (5×40 vol). The combined organic extracts were dried and evaporated to give the title compound as an off-white solid (80% th, 2 steps).

Workup

  1. concentrationthen concentrated
  2. additionWater (30 vol) was added
  3. extractionthe solution was extracted with ethyl acetate (3×20 vol)
  4. extractionthen extracted with dichloromethane (5×40 vol)
  5. customThe combined organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-966ccbaf97cf4e198a4ec66239090793
Source dataset
uspto-grants-2010_06
Patent number
US07732600B2

Linked notes

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