1-(4-Fluorophenyl)piperazine → 2-[2-[4-(4-fluorophenyl)-1-pyrazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one

HRID 235630Notes

Reaction equation

HRID 235630 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5]1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(OCC)(=O)C>[F:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH:27]=[CH:26][N:25]([CH2:2][CH2:3][CH:4]3[C:9](=[O:10])[NH:8][C:7]4[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=4[S:5]3)[CH:24]=[CH:23]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 752601-(4-Fluorophenyl)piperazineHCID 137846232-(2-bromoethyl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

Product 1

HCID 202201082-[2-[4-(4-fluorophenyl)-1-pyrazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In 20 ml of ethyl acetate were dissolved 1.36 g of 2-(2-bromoethyl)-2H-1,4-benzothiazin-3(4H)-one and 1.8 g of 1-(4-fluorophenyl)piperazine. The solvent was evaporated off, and the residue was stirred at 110° C. for one hour. The reaction product was extracted with ethyl acetate, and the extract was washed with water and dried over MgSO4. The crystals obtained by evaporation of the solvent were recrystallized from methanol to give 2-[2-[4-(4-fluorophenyl)-1-pyrazinyl]ethyl]-2H-1,4-benzothiazin-3(4H)-one as prisms, m.p. 158°-159° C. The yield was 0.94 g (50.5%).

Workup

  1. customThe solvent was evaporated off
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over MgSO4
  5. customThe crystals obtained by evaporation of the solvent
  6. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-8c226101b90a48d6a2efd64baa8aca18
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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