Cvt-2738 → N-(2,6-dimethylphenyl)-2-{4-[4-(2-methoxyphenyl)-3-oxobutyl]piperazin-1-yl}acetamide

HRID 230117Notes

Reaction equation

HRID 230117 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:18])[CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28](=[O:31])[CH:29]=[CH2:30]>C(O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[O:18])[CH2:11][N:12]1[CH2:13][CH2:14][N:15]([CH2:30][CH2:29][C:28](=[O:31])[CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH3:19])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 2608606Cvt-2738HCID 184526881-(2-Methoxyphenyl)but-3-en-2-one

Product 1

HCID 18452748N-(2,6-dimethylphenyl)-2-{4-[4-(2-methoxyphenyl)-3-oxobutyl]piperazin-1-yl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(2,6-dimethylphenyl)-2-piperazinylacetamide (100 mg, 0.4 mmol) and 1-(2-methoxyphenyl)but-3-en-2-one (100 mg, 0.56 mmol), a compound of formula (12), in ethanol (2 mL) was heated at reflux for 16 hours. Ethanol was removed under reduced pressure and the residue was purified by preparative TLC, using 10% methanol in dichloromethane as mobile phase, to afford N-(2,6-dimethylphenyl)-2-{4-[4-(2-methoxyphenyl)-3-oxobutyl]piperazin-1-yl}acetamide, a compound of formula (13).

Workup

  1. temperatureat reflux for 16 hours
  2. customEthanol was removed under reduced pressure
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-014f041ebe9647648c3653368e868722
Source dataset
uspto-grants-2009_07
Patent number
US07566717B2

Reaction notes

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