Piperidine → HCID 67601322, compound

HRID 1075676Notes

Reaction equation

HRID 1075676 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:19][C:20]1[C:29]2[N:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:23]([CH:30]=O)=[CH:22][CH:21]=1.N1CCCCC1>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[C:12]2=[CH:30][C:23]1[CH:22]=[CH:21][C:20]([OH:19])=[C:29]2[C:24]=1[CH:25]=[CH:26][CH:27]=[N:28]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 2753638-Hydroxyquinoline-5-carbaldehydeHCID 53971753tert-Butyl (2-oxoindolin-5-yl)carbamate

Product 1

HCID 67601322HCID 67601322, compoundYield 79.3%

Procedure

To a solution of 5-t-butoxycarbonylamino-2-oxindole (630 mg, 2.5 mmol) and 8-hydroxyquinoline-5-carbaldehyde (450 mg, 2.6 mmol) in absolute alcohol was added piperidine (0.26 g, 2.6 mmol). The reaction was carried out at 80° C. for 3 h. The solvent was evaporated and the residue was purified by silica gel chromatography (eluant cyclohexane/ethylacetate 2:3) thus giving 800 mg of 5-(t-butoxycarbonylamino)-3-(8-hydroxyquinol-5-ylmethylen)-2-oxindole.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography (eluant cyclohexane/ethylacetate 2:3)

Sources & evidence

ORD record
ord-7f62431646d54316b474cb59ad023cba
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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