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

HRID 344381

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+].BrCCCCC[C:34]1[CH:44]=[CH:43][CH:42]=[C:36]2[C:37]([NH:39][C:40](=[O:41])[C:35]=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]([CH2:18][CH2:3][CH2:4][CH2:5][CH2:37][N:39]3[C:40](=[O:41])[C:35]4[C:34](=[CH:44][CH:43]=[CH:42][CH:36]=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: 50 °C

Procedure

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide hydrochloride (23.0 g) was dissolved in dimethylformamide (250 ml). Potassium carbonate (28.5 g) and 5-bromopentylphthalimide (20.4 g) were added, and the mixture was stirred at 50° C. for 8 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 20.0 g of 4-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)pentyl)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-dfee23cb27344e6f8d8bc7c79bc37237
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05864039

Linked notes

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