Water → 6-[3-(4-(4-Fluorophenyl)-1-piperazinyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide

HRID 654105Notes

Reaction equation

HRID 654105 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.O>CN(C)C=O.C(OCC)(=O)C>[F:35][C:32]1[CH:31]=[CH:30][C:29]([N:26]2[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][CH2:20][N:9]3[C:8]4[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=4[C:6]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[S:10]3(=[O:12])=[O:11])[CH2:28][CH2:27]2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 7080916~{h}-Benzo[c][1,2]benzothiazine 5,5-DioxideHCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 198884536-[3-(4-(4-Fluorophenyl)-1-piperazinyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxideYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide (2 g) in dry N,N-dimethylformamide (15 cc) is added dropwise to a suspension of sodium hydride (0.27 g, 80% suspension in oil) in N,N-dimethylformamide (5 cc). After 30 minutes' stirring, a solution of 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine (2.2 g) in N,N-dimethylformamide (15 cc) is added. The reaction mixture is heated to 100° C. for 1 hour and 15 minutes and is then cooled and poured into a mixture of water (200 cc) and ethyl acetate (180 cc). The organic phase is washed with water (3×80 cc) is dried over magnesium sulphate and is concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from acetonitrile (60 cc); the crystals obtained are filtered off, washed with acetonitrile (5 cc) and dried. 6-[3-(4-(4-Fluorophenyl)-1-piperazinyl)propyl]-6H-dibenzo[c,e]-1,2-thiazine 5,5-dioxide (2.8 g) is obtained, melting at 163° C.

Workup

  1. temperatureis then cooled
  2. washThe organic phase is washed with water (3×80 cc)
  3. dry with materialis dried over magnesium sulphate
  4. concentrationis concentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is recrystallized from acetonitrile (60 cc)
  6. customthe crystals obtained
  7. filtrationare filtered off
  8. washwashed with acetonitrile (5 cc)
  9. customdried

Sources & evidence

ORD record
ord-f3f52e7000fe4c0b99214e24171af868
Source dataset
uspto-grants-1992_07
Patent number
US05130313

Reaction notes

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