Sodium hydride → HCID 14580056, compound

HRID 1493266Notes

Reaction equation

HRID 1493266 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, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The experiment is carried out as in Example 18, starting with 6-chloronaphtho[1,8-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 80dispersion 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 a 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)-1-piperazinyl]propyl}-naphtho[1,8-cd]isothiazole 1,1-dioxide (1.2 g) 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 a mixture of dichloromethane and ethyl acetate (95-5 vol) as eluant
  8. customrecrystallized

Sources & evidence

ORD record
ord-23eaaf79b3274521a64752439a0d3e84
Source dataset
uspto-grants-1991_06
Patent number
US05021420

Reaction notes

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