Piperidine → (Z)-Ethyl 3-{4-Oxo-2-[(2-oxoindolin-3-ylidene)methyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoate

HRID 597847Notes

Reaction equation

HRID 597847 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[C:15]2[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[NH:9][C:8]=1[CH:17]=O)[CH3:2].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29].N1CCCCC1>CCO>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[C:15]2[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[NH:9][C:8]=1/[CH:17]=[C:22]1\[C:21](=[O:29])[NH:20][C:28]2[C:23]\1=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 321710OxindoleHCID 46914013HCID 46914013, compound

Product 1

HCID 46847848(Z)-Ethyl 3-{4-Oxo-2-[(2-oxoindolin-3-ylidene)methyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 5 (0.50 mmol) and indolin-2-one (0.50 mmol) was added with EtOH (5.0 mL) and piperidine (0.1 mL). The reaction was heated at reflux for 12 h. The resultant precipitate was filtered and washed with EtOH to provide the diresed product. 1H NMR (CDCl3) δ 7.93 (s, 1 H), 7.61 (s, 1 H), 7.59 (d, 1 H, ArH), 7.19 (dd, 1 H), 7.09 (dd, 1 H), 6.89 (d, 1 H), 4.07 (q, 2 H), 3.27 (t, 2 H), 2.91 (t, 2 H), 2.74 (t, 2 H), 2.52 (t, 2 H), 2.14-2.19 (m, 2 H), 1.18 (t, 3 H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 12 h
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with EtOH
  5. customto provide the diresed product

Sources & evidence

ORD record
ord-95c278858c9f48bda48c0567547822f6
Source dataset
uspto-grants-2011_03
Patent number
US07897602B2

Reaction notes

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