N-bromobutanimide → 4-[2-(4-1,2-Benzisothiazol-3-YL-piperazin-1-YL)-ethyl]-2-bromo-phenylamine

HRID 2211876Notes

Reaction equation

HRID 2211876 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[N:2]1.[Br:25]N1C(=O)CCC1=O>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[C:22]([Br:25])[CH:23]=3)[CH2:14][CH2:15]2)=[N:2]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 219631764-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine

Product 1

HCID 219635064-[2-(4-1,2-Benzisothiazol-3-YL-piperazin-1-YL)-ethyl]-2-bromo-phenylamineYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2 dram vial was added 0.20 g (0.6 mmol) 4-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine, 6.0 mL CH2Cl2, and 104 mg (0.6 mmol) N-bromosuccinimide. The reaction was stirred for 30 min at rt and then quenched with 1 M Na2SO3. The organic layer was separated, dried, and concentrated in vacuo. The deep red product was purified by MPLC to give 0.059 g (24% yield) of a clear, tacky liquid. MS (APCI): 419 [M+H]+.

Workup

  1. customquenched with 1 M Na2SO3
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe deep red product was purified by MPLC
  6. customto give 0.059 g (24% yield) of a clear, tacky liquid

Sources & evidence

ORD record
ord-dd58841c491f4e2d88ad5cfaec167f1d
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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