Piperidine → N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]-2-piperidin-1-ylacetamide

HRID 1950067Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]([CH2:26][CH3:27])[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=2)[CH2:15]1)=[O:4].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:26]([N:5]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=2)[CH2:15]1)[C:3](=[O:4])[CH2:2][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:27]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloro-N-ethyl-N-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]acetamide (129 mg) in N,N-dimethylformamide (5 ml) were sequentially added piperidine (0.07 ml) and potassium carbonate (184 mg), and the solution was stirred overnight at 60° C. The solution was let to cool, then a saturated aqueous solution of sodium bicarbonate was added thereto, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous potassium carbonate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (139 mg).

Workup

temperatureto cool
extractionthe solution was extracted with ethyl acetate
washwashed with brine
dry with materialdried over anhydrous potassium carbonate
customthe solvent was evaporated in vacuo
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record: ord-1bee876f23744752a873b12b34ea78d8
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399520B2

Reaction notes

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