Hydrochloric Acid → 2-Methyl-5-(2-piperazin-1-ylethoxy)quinoline

HRID 1349938Notes

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[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[N:3]=1.Cl.C(OCC)C>C(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[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

tert-Butyl 4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazine-1-carboxylate (1.04 g, 2.8 mmol) was dissolved in ethanol (60 mL) and treated with 1M hydrochloric acid in diethyl ether (16 mL, 16 mmol) and stirred at 40° C. for 17 h. The reaction mixture was filtered and the white solid was collected and dried in vacuo. The hydrochloride salt precipitate was dissolved in water (25 mL) and potassium carbonate was added until the pH reached 10. The aqueous layer was washed with 5% methanol in dichloromethane (4×100 mL) then 10% methanol in dichloromethane (4×100 mL). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo, affording the title compound as a brown oil (0.69 g, 91%).

Workup

filtrationThe reaction mixture was filtered
customthe white solid was collected
customdried in vacuo
dissolutionThe hydrochloride salt precipitate was dissolved in water (25 mL)
additionpotassium carbonate was added until the pH
washThe aqueous layer was washed with 5% methanol in dichloromethane (4×100 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8410ae0fad3a4c40a60d2feac55f518d
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214674B2

Reaction notes

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