Piperidine → 5-Methoxyoxindole

HRID 2213673Notes

Reaction equation

HRID 2213673 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[NH:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]=O.N1CCCCC1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[CH:18][C:14]1[NH:13][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 13854Pyrrole-2-carboxaldehydeHCID 15142865-Methoxyoxindole

Product 2

HCID 15142865-MethoxyoxindoleHCID 69545137HCID 69545137, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

5-Methoxyindolin-2-one was prepared by the method of Crestini, C.; Saladino, R. Synth. Commun. (1994), Vol. 24, NO. 20, p. 2835. A solution of 5-methoxyindolin-2-one (0.41 g, 2.5 mmol) and 2-pyrrolecarboxaldehyde (0.25 g, 2.6 mmol) in ethanol (5 mL) was treated with piperidine (0.05 g, 0.65 mmol). The reaction mixture was then heated to 85° C. for 3 hours. The reaction was then cooled to ambient temperature and the reaction mixture was chromatographed on SiO2 (12 g) using 3:1 hexane/ethyl acetate to afford 5-methoxy-3-[(pyrrol-2-yl)methylene]indolin-2-one; (0.48 g); 1H NMR (400 MHz, DMSO-d6) δ 3.74 (s, 3H), 6.30 (m, 1H), 6.60–6.80 (m, 3H), 7.30 (m, 1H), 7.35 (m, 1H), 7.76 (m, 1H), 10.80 (s, 1H) ppm.

Workup

  1. temperatureThe reaction was then cooled to ambient temperature
  2. customthe reaction mixture was chromatographed on SiO2 (12 g)

Sources & evidence

ORD record
ord-e8f057e1b58b47cebe446e12b860de25
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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