Piperidine → 3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydroindole-2-one

HRID 1840499Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13]=1[CH:21]=O.N1CCCCC1>C(O)C>[CH3:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13]=1[CH:21]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-oxindole (133 mg), 3-methyl-indole-2-carbaldehyde (190 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (10 mg) in ethanol was heated in a sealed tube at 95° C. for 4 hours. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven for overnight to give 3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one.

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe solid was collected by vacuum filtration
washwashed with cold ethanol
customdried in vacuum oven for overnight

Sources & evidence

ORD record: ord-0bb1aa3efe4c4047a0051fab89fe35ea
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680335B2

Reaction notes

Loading…