Potassium Carbonate → 4-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344382

Reaction equation

Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].BrCCCCCC[C:35]1[CH:45]=[CH:44][CH:43]=[C:37]2[C:38]([NH:40][C:41](=[O:42])[C:36]=12)=O>CN(C)C=O>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:5][CH2:4][CH2:3][CH2:18][CH2:17][CH2:38][N:40]3[C:41](=[O:42])[C:36]4[C:35](=[CH:45][CH:44]=[CH:43][CH:37]=4)[C:22]3=[O:25])[CH2:15][CH2:16]2)=[O:8])=[C:5]([O:20][CH3:21])[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride (8.5 g) was dissolved in dimethylformamide (100 ml). Potassium carbonate (10.5 g) and 6-bromohexylphthalimide (7.2 g) were added, and the mixture was stirred at 70° C. for 16 hr. The reaction mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 4.2 g of 4-amino-5-chloro-N-(1-(6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexyl)-piperidin-4-ylmethyl)-2-methoxybenzamide.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionthe residue was extracted with ethyl acetate
dry with materialThe extract was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b0302d1f48d04f79a5fc161d508661df
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05864039

Linked notes

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