Water → (4-(4-Chlorophenoxy)piperidin-1-yl)(1-(2-morpholinoethyl)-1H-indol-5-yl)methanone

HRID 2170860Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH:19]=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH:19]=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of (4-(4-chlorophenoxy)piperidin-1-yl)(1H-indol-5-yl)methanone (30 mg, 0.085 mmol, Step-1) and sodium hydride (60% in oil, 6 mg, 0.25 mmol) in N,N-dimethylformamide (1.5 mL) was added 4-(2-chloroethyl)morpholine hydrochloride (35 mg, 0.19 mmol) at room temperature. Then the mixture was stirred at 70° C. for 2 hours. The mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic layer was washed with water (20 mL), and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 11.9 mg (30% yield) of the title compound.

Workup

extractionextracted with ethyl acetate (20 mL)
washThe organic layer was washed with water (20 mL)
dry with materialdried over sodium sulfate
customAfter removal of the solvent
customthe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Sources & evidence

ORD record: ord-9c95cf8f363749269574a4679e2d50af
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051296B2

Reaction notes

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