Water → tert-Butyl 4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazine-1-carboxylate

HRID 1295567Notes

Reaction equation

[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:15][CH2:16][O:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH3:28])=[N:23]2.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:28][C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][CH:26]=[CH:27][C:18]=2[O:17][CH2:16][CH2:15][N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[N:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

tert-Butyl piperazine-1-carboxylate (1.4 g, 7.52 mmol) was added to a mixture of 5-(2-bromoethoxy)-2-methylquinoline (2 g, 7.52 mmol) and potassium carbonate (4.16 g, 30.1 mmol) in N,N-dimethylformamide (20 mL). The reactants were heated at 70° C. for 16 h under an atmosphere of argon. The reaction mixture was poured into water (200 mL) and extracted into ethyl acetate (3×200 mL). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography, eluting with 30% ethyl acetate in hexane affording the title compound as a tan solid (1.04 g, 37%).

Workup

extractionextracted into ethyl acetate (3×200 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography
washeluting with 30% ethyl acetate in hexane affording the title compound as a tan solid (1.04 g, 37%)

Sources & evidence

ORD record: ord-392fba9cc81c483a9b65486207c67540
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244726B2

Reaction notes

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