1-(2-Methoxyphenyl)piperazine → HCID 13784664, compound

HRID 235629Notes

Reaction equation

HRID 235629 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[S:6]1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CN(C)C=O>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:2][CH2:3][CH2:4][CH:5]2[C:10](=[O:11])[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6]2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 13784628HCID 13784628, compound

Product 1

HCID 13784664HCID 13784664, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 10 ml of dimethylformamide were dissolved 1.6 g of 2-(3-chloropropyl)-2H-1,4-benzothiazin-3(4H)-one and 2.55 g of 1-(2-methoxyphenyl)piperazine. The solution was stirred at 100° C. for 1.5 hour. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over MgSO4, then concentrated under reduced pressure. The concentrate was subjected to a column chromatography on silica-gel (150 g). From the eluate with hexane-acetone (2:1, v/v) was obtained 0.7 g of 2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-2H-1,4-benzothiazin-3(4H)-one as an oily substance. The 3/2 oxalate of this product was obtained as crystals, which were recrystallized from methanol and dichloromethane to give colorless prisms. The yield was 470 mg (13.3%), m.p. 202°-204° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c496464800148e1a22c2a96767171be
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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