Sodium hydride → HCID 14580056, compound

HRID 1087493Notes

Reaction equation

HRID 1087493 reaction equation
[Cl:1][C:2]1[C:3]2[C:11]3[C:10](=[CH:12][CH:13]=1)[S:9](=[O:15])(=[O:14])[NH:8][C:7]=3[CH:6]=[CH:5][CH:4]=2.Cl[CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:3]2[C:11]3[C:10](=[CH:12][CH:13]=1)[S:9](=[O:15])(=[O:14])[N:8]([CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[CH2:22][CH2:21]1)[C:7]=3[CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazineHCID 14580055HCID 14580055, compound

Product 1

HCID 14580056HCID 14580056, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The experiment is carried out as in Example 18, starting with 6-chloronaphtho[l,8-cd]isothiazole 1,1-dioxide (1.4 g), 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine (1.5 g), sodium hydride (0.18 g) in an 80% dispersion in vaseline oil and dimethylformamide (15 cc). The reaction mixture is heated for 1 hour 30 minutes at 90° C., cooled to a temperature of about 20° C. and then concentrated to dryness at 60° C. under reduced pressure (0.5 mm Hg; 0.07 kPa). The residue is redissolved in dichloromethane (50 cc) and the solution is washed with distilled water (20 cc), dried over magnesium sulphate and concentrated to dryness at 20° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is purified by chromatography on a silica column with mixture of dichloromethane and ethyl acetate (95-5 vol) as eluant, then recrystallized from boiling acetonitrile (10 cc). 6-Chloro-2-{3-[4-(4-fluorophenyl)-l-piperazinyl]propyl}naphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 is obtained, m.p. 125° C.

Workup

  1. temperaturecooled to a temperature of about 20° C.
  2. concentrationconcentrated to dryness at 60° C. under reduced pressure (0.5 mm Hg; 0.07 kPa)
  3. dissolutionThe residue is redissolved in dichloromethane (50 cc)
  4. washthe solution is washed with distilled water (20 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness at 20° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  7. customThe residue is purified by chromatography on a silica column with mixture of dichloromethane and ethyl acetate (95-5 vol) as eluant
  8. customrecrystallized

Sources & evidence

ORD record
ord-25fc9194963f49c2aee38bdc2d72932f
Source dataset
uspto-grants-1991_07
Patent number
US05036075

Reaction notes

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