5-(Dimethylamino)-2-nitrobenzoic acid → 5-dimethylamino-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362897Notes

Reaction equation

[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8]([OH:10])=O.[NH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:15][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8]([NH:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:20][CH2:19]1)=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Step 1): A mixture of 5-dimethylamino-2-nitrobenzoic acid [J. Med. Chem., 24, 742 (1981)](9.0 g, 40 mmol), 4-aminomethyl-1-diphenylmethylpiperidine (12.0 g, 40 mmol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimido hydrochloride (WSC) (8.0 g, 40 mmol) and 4-dimethylaminopyridine (DMAP) (5 g, 40 mmol) in dichloromethane (400 ml) was stirred at 0° C. for 1 hour, then at room temperature for 3 days. The reaction mixture was washed with 1N HCl, then water. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (5% methanol in dichloromethane) to give 5-dimethylamino-2-nitro-N-[(1-diphenylmethyl-piperidin-4-yl)methyl]benzamide (47%) as yellow solid: mp 200° C.

Workup

waitat room temperature for 3 days
washThe reaction mixture was washed with 1N HCl
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-f7ef305cc63a43e1af4ce8701b928c93
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872115

Reaction notes

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