Triethylamine → [4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-acetonitrile

HRID 1433071Notes

Reaction equation

HRID 1433071 reaction equation
[N:1]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(CC)CC.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([S:26](Cl)(=[O:28])=[O:27])[S:23][C:22]=2[CH:30]=1>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:25]=[C:24]([S:26]([N:4]3[CH2:5][CH2:6][N:1]([CH2:7][C:8]#[N:9])[CH2:2][CH2:3]3)(=[O:28])=[O:27])[S:23][C:22]=2[CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 15522031(Piperazin-1-yl)acetonitrile

Product 1

HCID 86592559[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperazin-1-yl-acetonitrile (0.32 g, 2.3 mmol) and Et3N (350 mg, 3.4 mmol) is added 6-chloro-benzo[b]thiophene-2-sulfonyl chloride (615 mg, 2.3 mmol) at 0° C. The reaction is warmed to room temperature and stirred 4 h. The reaction is diluted with CH2Cl2, washed with 1 N HCl, NaHCO3 and dried over MgSO4. The solution is concentrated and the residue is triturated with PE, triturated with Et2O, and pumped to yield [4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-acetonitrile which can be used without further purification. 1H NMR (300 MHz, CDCl3) δ7.89-7.84 (m, 3H), 7.48 (dd, 1H), 4.36 (s, 2H), 3.92 (s, 2H), 3.64-3.61 (m, 2H), 3.57-3.54 (m, 2H); MS (Ion Spray) 444 (M+H)+.

Workup

  1. washwashed with 1 N HCl, NaHCO3
  2. dry with materialdried over MgSO4
  3. concentrationThe solution is concentrated
  4. customthe residue is triturated with PE
  5. customtriturated with Et2O

Sources & evidence

ORD record
ord-099fec0ac2c14f1c89912ea4c55b36e6
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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