Potassium Carbonate → 4-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholine

HRID 1925343Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-6-methoxyquinolin-7-ol (1.0 g, 4.77 mmol) and 4-(3-chloropropyl)morpholine (0.86 g, 5.25 mmol)in DMF (9.5 mL), was added potassium carbonate (2.0 g, 14.3 mmol). The mixture was heated to 90° C. for 15 h. After cooling RT, the mixture was diluted with H2O (30 mL). The mixture was extracted with EtOAc (3×25 mL) and the organic extracts were washed with H2O and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (5% MeOH/CH2Cl2) to yield the title compounds as a light yellow solid. MS (ESI, pos. ion) m/z: 337 (M+1). Mass Calc'd for C17H22ClN2O3: 336.1.

Workup

temperatureAfter cooling RT
extractionThe mixture was extracted with EtOAc (3×25 mL)
washthe organic extracts were washed with H2O and brine
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-6144049c1c86474187d26e7b7092801f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178557B2

Reaction notes

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