Potassium Iodide → N-{4-[2-(4-Benzo[D]isothiazol-3-YL-piperazin-1-YL)-ethyl]-5-chloro-2-methyl-phenyl}-N-methyl-acetamide

HRID 2211909Notes

Reaction equation

HRID 2211909 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:14])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:15])[CH:5]=1.[ClH:16].[N:17]1([C:23]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[S:25][N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.O.C(Cl)Cl>[S:25]1[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:23]([N:17]2[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][C:4]3[C:9]([Cl:16])=[CH:8][C:7]([N:10]([CH3:14])[C:11](=[O:13])[CH3:12])=[C:6]([CH3:15])[CH:5]=3)[CH2:19][CH2:18]2)=[N:24]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21963208N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-methyl-acetamide

Product 1

HCID 10456064N-{4-[2-(4-Benzo[D]isothiazol-3-YL-piperazin-1-YL)-ethyl]-5-chloro-2-methyl-phenyl}-N-methyl-acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

N-[4-(2-chloro-ethyl)-2-methyl-phenyl]-N-methyl-acetamide (0.300 g, 1.153 mmol), 3-piperazin-1-yl-benzo[d]isothiazole hydrochloride (0.442 g, 1.729 mmol), potassium carbonate (0.237 g, 1.729 mmol), and potassium iodide (0.173 g, 1.153 mmol) in acetonitrile (3.5 mL) was subjected to 150° C. for 30 min. under microwave assistance using a Smith Personal Chemistry microwave. The reaction was diluted with H2O (50 mL) and CH2Cl2 (100 mL). The layers were separated and the organics washed with 1 N HCl (2×25 mL). The aqueous layer was made basic and extracted with CH2Cl2 (3×50 mL). The organics were dried (MgSO4), and concentrated to a solid residue. The residue was subjected to chromatography (MeOH:CH2Cl2 1:19) and collected as an amorphous residue and taken up in 1,4-dioxane and subjected to HCl gas for 10 min. The resulting solid was collected by filtration and dried at 50° C. under high vacuum overnight (0.770 g). 100% purity at 254 nm; LCMS (APCI): 409.2 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organics washed with 1 N HCl (2×25 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated to a solid residue
  6. customcollected as an amorphous residue
  7. filtrationThe resulting solid was collected by filtration
  8. customdried at 50° C. under high vacuum overnight (0.770 g)

Sources & evidence

ORD record
ord-73ae26c538f24183a4240c2ef0326c38
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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