Formaldehyde → 1-Piperidin-1-ylmethyl-3-(1-H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one

HRID 47236

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[C:8](=[O:16])[NH:9][C:10]2[C:15]\1=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=O.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>CCO>[N:19]1([CH2:17][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[CH:6][C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)[C:8]2=[O:16])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (0.60 g, 2.85 mmol), paraformaldehyde (0.13 g, 4.28 mmol) and piperidine (0.24 g, 2.85 mmol) in EtOH (5 mL) was heated to 60-70° C. for 14 h. The reaction mixture was cooled to −20° C. for 1 h and the fine yellow solid present was collected by filtration. The solid collected was dried under vacuum to give the title compound as a yellow solid (0.68 g, 77%).

Workup

filtrationthe fine yellow solid present was collected by filtration
customThe solid collected
customwas dried under vacuum

Sources & evidence

ORD record: ord-5d2d2ccee1e04d0e820bbbc0fb7a0faa
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699863B1

Linked notes

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