Potassium Carbonate → HCID 19418919, compound

HRID 864356Notes

Reaction equation

HRID 864356 reaction equation
[NH:1]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[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:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[S:10](=[O:18])(=[O:17])[N:9]=3)[CH2:28][CH2:27]2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6869021,1-Dioxo-N-phenyl-1,2-benzothiazol-3-amineHCID 106825561-(3-Chloropropyl)-4-(4-fluorophenyl)piperazine

Product 1

HCID 19418919HCID 19418919, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2.2 g of 3-anilino-1,2-benzisothiazole 1,1-dioxide, 2.1 g of 1-(3-chloropropyl)-4-(4-fluorophenyl)piperazine, 3.4 g of potassium carbonate, 1.1 g of tetrabutylammonium bromide and 25 cm3 of dimethylformamide is refluxed for 24 hours. The mixture is then cooled to a temperature of about 20° C. The filtrate is evaporated to dryness at 40° C. under reduced pressure (10 mm of mercury; 1.35 kPa). The residue is taken up in 20 cm3 of water and extracted with 75 cm3 of dichloromethane. The organic phase thus obtained is dried over anhydrous magnesium-sulphate and evaporated to dryness at 40° C. under reduced pressure (20 mm of mercury; 2.7 kPa). The oil obtained is purified by flash chromatography on a silica column, under a nitrogen stream at moderate pressure (0.1-1.5 bar) with ethyl acetate as eluent. 1.0 g of a beige meringue is obtained which, when recrystallization from 10 cm3 of hot ethanol yields 0.95 g of 3-{{3-[4-(4-fluorophenyl)-1-piperazinyl]propyl}phenylamino}-1,2-benzisothiazole 1,1-dioxide; melting point =134° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. customThe filtrate is evaporated to dryness at 40° C. under reduced pressure (10 mm of mercury; 1.35 kPa)
  3. extractionextracted with 75 cm3 of dichloromethane
  4. customThe organic phase thus obtained
  5. dry with materialis dried over anhydrous magnesium-sulphate
  6. customevaporated to dryness at 40° C. under reduced pressure (20 mm of mercury; 2.7 kPa)
  7. customThe oil obtained
  8. customis purified by flash chromatography on a silica column, under a nitrogen stream at moderate pressure (0.1-1.5 bar) with ethyl acetate as eluent
  9. custom1.0 g of a beige meringue is obtained
  10. customwhich, when recrystallization from 10 cm3 of hot ethanol

Sources & evidence

ORD record
ord-90265b04bd484ec1ab8ab45084b141c5
Source dataset
uspto-grants-1996_10
Patent number
US05563144

Reaction notes

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