Phenol → HCID 15016114, compound

HRID 2226109Notes

Reaction equation

HRID 2226109 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:33])[CH:25](Cl)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:19]1>CN(C=O)C>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:33])[CH:25]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 3622053Piperazine, 1-(chlorophenylacetyl)-4-(2-methoxyphenyl)-

Product 1

HCID 15016114HCID 15016114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride 80% dispersion in oil (1.7 g) was added to dry DMF (100 ml) under argon. Phenol (3.76 g; 0.04 m) was added over 20 mins and the resulting grey mixture was stirred a further 20 mins and cooled to 0° C. A solution of 1-(2-methoxyphenyl)-4-(1-oxo-2-chloro-2-phenylethyl)piperazine (13.8 g; 0.04 m) in dry DMF (60 ml) was added over 20 mins. The mixture was heated to 60° C. over a period of about 3 hrs and then maintained at 60° C. for 21/2 hrs and then stirred at ambient temperature overnight. The mix was cooled to 0° C., treated with 10 ml crushed ice and the DMF was vacuumed off. The residue, in methylene chloride, was washed well with water and dried over magnesium sulphate. The oil resulting on evaporation, solidified on standing for a few days to give 1-(2-methoxyphenyl)-4 -(1-oxo-2-phenoxy-2-phenylethyl)piperazine.

Workup

  1. temperatureThe mixture was heated to 60° C. over a period of about 3 hrs
  2. temperaturemaintained at 60° C. for 21/2 hrs
  3. stirringstirred at ambient temperature overnight
  4. temperatureThe mix was cooled to 0° C.
  5. additiontreated with 10 ml
  6. customcrushed ice
  7. washThe residue, in methylene chloride, was washed well with water
  8. dry with materialdried over magnesium sulphate
  9. customThe oil resulting on evaporation
  10. waiton standing for a few days

Sources & evidence

ORD record
ord-acb67f5fcc59479ba99edd53bd79c9ff
Source dataset
uspto-grants-1994_09
Patent number
US05346896

Reaction notes

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