Triethylamine → 2-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, hydrochloride

HRID 569579Notes

Reaction equation

HRID 569579 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[S:7]1(=[O:17])=[O:16].Cl.[Cl:19][C:20]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[N:22][CH:21]=1.C(N(CC)CC)C.C(OC(=O)C)C>CN(C)C=O.C(Cl)Cl>[ClH:1].[Cl:19][C:20]1[N:25]=[C:24]([N:26]2[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]4[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=4[S:7]3(=[O:17])=[O:16])[CH2:30][CH2:31]2)[CH:23]=[N:22][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 198421MK-212 hydrochlorideHCID 132898002-(4-Chloro-1-butyl)-3(2H)-benz[d]isothiazolone 1,1-Dioxide

Product 1

HCID 452592292-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared by dissolving 2.5 g (0.008 mol) of 2-(4-chlorobutyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide in 50 ml of dimethylformamide and to that solution 2.5 g (0.01 mol) of 1-(6-chloro-2-pyrazinyl)piperazine hydrochloride and 5 ml of triethylamine are added. Stirring is continued for 48 hours. The solvent is removed under reduced pressure and the residue is partitioned between water and methylene chloride. The methylene chloride extracts are combined, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give crude base. Preparative HPLC (silica gel; ethylacetate:methylene chloride (9.1)) gives, following evaporation of the appropriate fractions (Rf 0.5), the title compound, which is converted to the hydrochloride salt; mp 246°-249° C.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is partitioned between water and methylene chloride
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give crude base
  7. customevaporation of the appropriate fractions (Rf 0.5)

Sources & evidence

ORD record
ord-cf61ccd3c59a4cc8baa6b3161cc521c8
Source dataset
uspto-grants-1988_03
Patent number
US04732984

Reaction notes

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