Triethylamine → 1-(6-Chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazine

HRID 379561Notes

Reaction equation

HRID 379561 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(N(CC)CC)C.[I:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:16][CH2:17][N:18]([C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([I:28])=[CH:30][CH:31]=3)[CH2:19][CH2:20]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 113588251-((6-Chloronaphthalen-2-yl)sulfonyl)piperazine

Product 1

HCID 223297181-(6-Chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazineYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1(6-Chloronaphth-2-ylsulphonyl)piperazine (0.65 g, 2.1 mmol) was dissolved in dichloromethane (50 mL) and triethylamine (2.9 mL, 21 mmol) was added at room temperature. 4-Iodobenzoyl chloride (0.56 g, 2.1 mmol) was added as a solid in one portion and the reaction mixture stirred for one hour at room temperature. The reaction mixture was concentrated in vacuo, then separated between EtOAc (100 mL) and saturated sodium hydrogen carbonate solution (100 mL). The EtOAc layer was separated, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was subjected to chromatography (SiO2: 50% EtOAc/Hexane) to yield 1-(6-chloronaphth-2-ylsulphonyl)-4-(4-iodobenzoyl)piperazine as a white solid (0.97 g); 1H NMR (DMSO-d6) δ=3.05 ppm (s,4H) δ=3.53 ppm (s,4H), δ=7.11 ppm & 7.74 ppm (dd,4H), δ=7.65 to 7.84 ppm (m,2H) δ=8.10 ppm to 8.28 ppm (m,3H), δ=8.47 ppm (s,1H); MS (M+H)+ 540.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customseparated between EtOAc (100 mL) and saturated sodium hydrogen carbonate solution (100 mL)
  3. customThe EtOAc layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57044ca47636410e8924715caf9be3a5
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

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