Benzenamine, 4-(4-morpholinyl)- → HCID 178474211, compound

HRID 2352804Notes

Reaction equation

O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:24].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:28][CH:27]=1>O1CCOCC1>[N:32]1([C:29]2[CH:28]=[CH:27][C:26]([NH:25][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([C:14]5[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:24])=[CH:31][CH:30]=2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 100 °C

Procedure

A dry 50 mL flask was charged with N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-acetamide (prepared below, 70 mg, 0.217 mmol) and Dioxane (10 mL). To the resulting solution was added N-(4-aminophenyl)morpholine (200 mg, 1.122 mmol), and the mixture was stirred for 24 h at 100° C. Subsequently, the reaction mixture was cooled to room temperature. The resulting suspension was concentrated in vacuo and the resulting solid residue was recrystallized from iPrOH (˜5 mL). The solid recovered through filtration then was subjected to flash silica gel chromatography using a 5% MeOH/CHCl3 eluant mixture to afford the title compound in 33% yield (35 mg, 0.072 mmol).

Workup

temperatureSubsequently, the reaction mixture was cooled to room temperature
concentrationThe resulting suspension was concentrated in vacuo
customthe resulting solid residue was recrystallized from iPrOH (˜5 mL)
filtrationThe solid recovered through filtration

Sources & evidence

ORD record: ord-101ef7cb2d6b40ce8b71a430ed05948d
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

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