3-(Cyclopentyloxy)-4-methoxyaniline → 1-Benzyl-4-(3-cyclopentyloxy-4-methoxyanilino)-1,2,5,6-tetrahydropyridin-2-one

HRID 1977600Notes

Reaction equation

HRID 1977600 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[NH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][C:24]1=[O:30])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1>[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([NH:10][C:9]2[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)=[CH:25][C:24]1=[O:30])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 27793343-(Cyclopentyloxy)-4-methoxyanilineHCID 224955411-Benzylpiperidine-2,4-dione

Product 1

HCID 101573561-Benzyl-4-(3-cyclopentyloxy-4-methoxyanilino)-1,2,5,6-tetrahydropyridin-2-oneYield 80.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.50 g (2.41 mmole) of 3-cyclopentyloxy-4-methoxyaniline produced in Example 1(2) and 0.49 g (2.41 mmole) of 1-benzyl-2,4-dioxopiperidine were dissolved in 20 ml of benzene and the mixture was stirred at room temperature for 20 hours. After the reaction, the precipitated crystal was collected by filtration and washed with benzene, then was dried in vacuo to obtain the title compound 0.76 g (yield 80.6%) as a light pink solid.

Workup

  1. customAfter the reaction
  2. filtrationthe precipitated crystal was collected by filtration
  3. washwashed with benzene
  4. customwas dried in vacuo

Sources & evidence

ORD record
ord-57e1909d80274cf991dd4cba2d7dd98a
Source dataset
uspto-grants-2001_05
Patent number
US06235736B1

Reaction notes

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