Triethylamine → HCID 13135434, compound

HRID 1648784Notes

Reaction equation

HRID 1648784 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[C:21]([NH:24][C:25]1[CH:44]=[CH:43][C:28]([O:29][CH2:30][CH2:31]OS(C2C=CC(C)=CC=2)(=O)=O)=[C:27]([O:45][CH3:46])[CH:26]=1)(=[O:23])[CH3:22]>CN(C)C=O>[C:21]([NH:24][C:25]1[CH:44]=[CH:43][C:28]([O:29][CH2:30][CH2:31][N:11]2[CH2:12][CH2:13][N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[CH2:9][CH2:10]2)=[C:27]([O:45][CH3:46])[CH:26]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 705291-(2-Fluorophenyl)piperazineHCID 12838086HCID 12838086, compound

Product 1

HCID 13135434HCID 13135434, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.07 g of 4-(2-fluorophenyl)piperazine and 1.5 ml of triethylamine are added to a solution of 1.5 g of 2-(4-acetamido-2-methoxyphenoxy)-1-(p-toluenesulfonyloxy)ethane in 10 ml of anhydrous dimethylformamide, and the mixture is stirred at 100° C. for 6 hours. After the reaction, the mixture is poured into ice-water, and the aqueous mixture is extracted with chloroform. The extract is washed with water and an aqueous saturated sodium chloride solution, successively. Said extract is dried and then evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel chromatography (Solvent; 2% methoanol/chloroform), and then recrystallized from a mixture of ethyl acetate and n-hexane. 1.3 g of 1-[2-(4-acetamido-2-methoxyphenoxy)ethyl]-4-(2-fluorophenyl)-piperazine are thereby obtained as colorless scales. Yield: 85%

Workup

  1. customAfter the reaction
  2. extractionthe aqueous mixture is extracted with chloroform
  3. washThe extract is washed with water
  4. extractionSaid extract
  5. customis dried
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel chromatography (Solvent; 2% methoanol/chloroform)
  9. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-e435c82100824a83818ed61f321ad259
Source dataset
uspto-grants-1983_11
Patent number
US04413006

Reaction notes

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