Toluene → 4-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344236

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(=O)([O-])[O-].[K+].[K+].BrCCCC[C:33]1[CH:43]=[CH:42][CH:41]=[C:35]2[C:36]([NH:38][C:39](=[O:40])[C:34]=12)=[O:37].[C:44]1(C)[CH:49]=CC=[CH:46][CH:45]=1>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]([CH2:49][CH2:44][CH2:45][CH2:46][N:38]3[C:39](=[O:40])[C:34]4[C:35](=[CH:41][CH:42]=[CH:43][CH:33]=4)[C:36]3=[O:37])[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 (15.0 g) was dissolved in dimethylformamide (100 ml) and toluene (150 ml), and potassium carbonate (18.6 g) and 4-bromobutylphthalimide (12.7 g) were added. The mixture was stirred at 70° C. for 2 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 13.6 g of 4-amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1 H-isoindol-2-yl)butyl)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-eeb7d60d72004466b26be8d8e8d440da
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05864039

Linked notes

Loading…