1-(4-Fluorophenyl)piperazine → 2-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one

HRID 235628Notes

Reaction equation

HRID 235628 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[C:13]([CH3:17])[C:14]([CH3:16])=[CH:15][C:7]=2[S:6]1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1>C(OCC)(=O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][CH:5]3[C:10](=[O:11])[NH:9][C:8]4[CH:12]=[C:13]([CH3:17])[C:14]([CH3:16])=[CH:15][C:7]=4[S:6]3)[CH2:27][CH2:26]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 752601-(4-Fluorophenyl)piperazineHCID 137846132-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 137846402-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-oneYield 78.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In 10 ml of ethyl acetate were dissolved 628 mg of 2-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one and 721 mg of 1-(4-fluorophenyl)piperazine. The solution was concentrated and the concentrate was stirred at 110° C. for one hour, diluted with water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over MgSO4 and concentrated to give 2-[3-[4-(4-fluorophenyl)-1-piperazinyl]propyl]-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one (650 mg, 78.6%). Recrystallization from methanol gave colorless prisms, m.p. 161°-162° C.

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-00d3682dc3a84113a1e9543fe0a112b5
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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