4-[3-(1-Piperidinyl)propoxy]aniline → 6-(3-methoxyphenyl)-3-[[4-(3-piperidin-1-ylpropoxy)anilino]methylidene]-1H-indol-2-one

HRID 11544Notes

Reaction equation

HRID 11544 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:20].[N:21]1([CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>O1CCCC1>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:8]2[CH:7]=[C:6]3[C:11]([C:3](=[CH:2][NH:37][C:34]4[CH:35]=[CH:36][C:31]([O:30][CH2:29][CH2:28][CH2:27][N:21]5[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]5)=[CH:32][CH:33]=4)[C:4](=[O:20])[NH:5]3)=[CH:10][CH:9]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 219749324-[3-(1-Piperidinyl)propoxy]anilineHCID 178418992HCID 178418992, compound

Product 1

HCID 1784189486-(3-methoxyphenyl)-3-[[4-(3-piperidin-1-ylpropoxy)anilino]methylidene]-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The named compound is prepared by refluxing 0.020 gms E & Z 3-hydroxymethylene-6-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one (see example 268) with 0.0375 gms 4-(3-piperidin-1-yl-propoxy)-phenylamine (used in the preparation of Example 218) in tetrahydrofuran (0.33 mL) for 36 h. Following cooling to room temperature, solvent evaporation in vacuo, trituration with isopropanol and filtration the reaction yields the named compound as a solid in the amount of 16.8 mg.

Workup

  1. customThe named compound is prepared
  2. customsolvent evaporation in vacuo, trituration
  3. filtrationwith isopropanol and filtration the reaction

Sources & evidence

ORD record
ord-76889c47bc604c94bffd53a4958f5462
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Reaction notes

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