Piperidine → HCID 86682014, compound

HRID 1749843Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[CH2:9][O:10][C:6]=2[C:5]=1[CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH3:2].[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH:37]=O)=[CH:29]1.N1CCCCC1>CO>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](/[CH:37]=[C:9]2\[O:10][C:6]3[C:5]([CH2:14][N:15]4[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20]4)=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=[CH:12][C:7]=3[C:8]\2=[O:11])=[CH:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of tert-butyl 4-[(6-ethoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.138 g, 0.367 mmol) in methanol (1.5 mL) was added with indole-3-carboxaldehyde (0.0553 g, 0.367 mmol) and piperidine (0.0250 g, 0.294 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the precipitated solid was collected by filtration to obtain tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-ethoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.137 g, 74%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-1e6acccd3b0d432e858170dd3d1c1596
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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