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

HRID 344379

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+].BrCCC[C:32]1[CH:33]=[C:34]2[C:39](=[O:40])[NH:38][C:36](=[O:37])[C:35]2=[CH:41][CH:42]=1.[C:43]1(C)[CH:48]=CC=C[CH:44]=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]([CH2:44][CH2:43][CH2:48][N:38]3[C:39](=[O:40])[C:34]4[C:35](=[CH:41][CH:42]=[CH:32][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 (8.0 g) was dissolved in dimethylformamide (100 ml) and toluene (100 ml). Potassium carbonate (9.9 g) and 4-bromopropylphthalimide (6.4 g) were added, and the mixture was stirred at 70° C. for 5 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 4.0 g of 4-amino-5-chloro-N-(1-(3-(2,3-dihydro-1,3-dioxo-1 H-isoindol-2-yl)propyl)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-6a3e8d330004481f8b19372b69962fa9
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05864039

Linked notes

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