Acetyl chloride → N-{4-[2-(4-1,2-Benzisothiazol-3-YL-piperazin-1-YL)-ethyl]-2-bromo-phenyl}-acetamide

HRID 2211877Notes

Reaction equation

HRID 2211877 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])=[C:20]([Br:25])[CH:19]=3)[CH2:12][CH2:11]2)=[N:2]1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>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[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:33](=[O:35])[CH3:34])=[C:20]([Br:25])[CH:19]=3)[CH2:12][CH2:11]2)=[N:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 219635064-[2-(4-1,2-Benzisothiazol-3-YL-piperazin-1-YL)-ethyl]-2-bromo-phenylamine

Product 1

HCID 21963447N-{4-[2-(4-1,2-Benzisothiazol-3-YL-piperazin-1-YL)-ethyl]-2-bromo-phenyl}-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2 dram vial was charged with 0.09 g (0.2 mmol) of 4-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-2-bromo-phenylamine and 0.87 mL CH2Cl2. This mixture was treated with 36 μL triethylamine (0.26 mmol) and 17 μL acetyl chloride and stirred at rt for 15 h. The reaction was quenched with aqueous 1M NaHCO3, the organic layer separated, dried, and concentrated in vacuo. This gave a quantitative yield of the desired product as a white solid. MS (APCI): 461 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8 Hz, 1H), 7.77 (d, J=8 Hz, 1H), 7.43 (t, J=7.5 Hz, 1H), 7.32 (t, J=7.5 Hz, 1H), 7.26 (s, 1H), 6.95–6.93 (m, 1H), 6.7 (d, J=8 Hz, 1H), 3.98 (br s, 2H), 3.57–3.55 (m, 4H), 2.72–2.58 (m, 8H).

Workup

  1. customThe reaction was quenched with aqueous 1M NaHCO3
  2. customthe organic layer separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dd1994dd85547a2b83f0b0275f55f57
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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