Piperidine → HCID 71278610, compound

HRID 1749767Notes

Reaction equation

HRID 1749767 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.[S:20]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[CH:31]1)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21].N1CCCCC1>CO>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])/[C:7](=[CH:39]/[C:32]3[C:33]4[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:30]([S:20]([C:23]4[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=4)(=[O:22])=[O:21])[CH:31]=3)/[O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeHCID 71278947HCID 71278947, compound

Product 1

HCID 71278610HCID 71278610, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 6-hydroxy-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3(2H)-one (0.525 g, 2.00 mol) in methanol (10 mL) was added with 1-tosyl-1H-indole-3-carboxaldehyde (0.599 g, 2.00 mmol) and piperidine (0.017 g, 0.200 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was added with methanol, and the solid was suspended in methanol and thereby washed to obtain the objective (Z)-6-hydroxy-7-[(4-methylpiperazin-1-yl)methyl]-2-[(1-tosyl-1H-indol-3-yl)methylene]benzofuran-3(2H)-one (0.887 g, 81%).

Workup

  1. washwashed

Sources & evidence

ORD record
ord-0fb1e604da684836bd60fa143845e119
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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