2-Dimethylaminopyridine → HCID 22909777, compound

HRID 1379168Notes

Reaction equation

HRID 1379168 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]Br)=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.CN(C1C=CC=CN=1)C>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 31268PyrrolidineHCID 22909785HCID 22909785, compound

Product 1

HCID 22909777HCID 22909777, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.10 g (0.23 mmol) of N-{3-(3,4-dimethylphenyl)propyl}-4-(2-bromoethoxy)-3-methoxyphenylacetamide obtained in Step 5 of Example 3, 0.16 g (2.3 mmol) of pyrrolidine and a catalytic amount of dimethylaminopyridine were dissolved in 10 ml of benzene, and the mixture was refluxed for 5 hours. After removing the solvent under a reduced pressure, the residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:1) to obtain the title compound.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customAfter removing the solvent under a reduced pressure

Sources & evidence

ORD record
ord-58674c3a4f694269ac3d72158d5c2170
Source dataset
uspto-grants-1997_09
Patent number
US05670546

Reaction notes

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