Dichloromethane → HCID 22329755, compound

HRID 379562Notes

Reaction equation

HRID 379562 reaction equation
[CH3:1][C:2]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=[CH:12][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].Cl[C:23]1[CH:24]=[C:25]2[C:30](=CC=1)[C:29]([S:33](Cl)(=[O:35])=[O:34])=[CH:28][CH:27]=[CH:26]2.[CH2:37](N(CC)CC)C.Cl[CH2:45][Cl:46]>>[Cl:46][C:45]1[CH:37]=[C:26]2[C:25](=[CH:24][CH:23]=1)[CH:30]=[C:29]([S:33]([N:9]1[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C:3]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:15][C:2]=3[CH3:1])[CH2:7][CH2:8]1)(=[O:34])=[O:35])[CH:28]=[CH:27]2

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 139221186-Chloronaphthalene-1-sulfonyl chlorideHCID 22329725HCID 22329725, compound

Product 1

HCID 22329755HCID 22329755, compound

Procedure

4-(2-Methyl-4-(3-pyridyl)benzoyl)piperazine (0.41 g, 1.5 mmol) was dissolved in dichloromethane (50 mL) at room temperature. 6-Chloronaphthalenesulphonyl chloride (0.38 g, 1.5 mmol) and triethylamine (1 ml, 7.5 mmol) were added and the reaction mixture stirred overnight. The reaction mixture was concentrated in vacuo. The crude product was dissloved in EtOAc (100 mL) and washed with saturated sodium hydrogen carbonate solution (100 mL). The EtOAc layer was separated, dried over MgSO4, filtered and concentrated in vacuo. The resulting solid was subjected to chromatography (SiO2: 50%, 60% EtOAc/Hexane) to yield 1-(6-chloronaphth-2-ylsulphonyl)-4-[2-methyl-4-(3-pyridyl)benzoyl]piperazine as a white solid (508.4 mg); 1H NMR (DMSO-d6) δ=2.15 ppm (s,3H), δ=2.94 to 3.25 ppm (m,6H), δ=3.78 ppm (m,2H), δ=7.23 ppm (d,1H), δ=7.44 to 7.62 ppm (m,3H), δ=7.70 ppm (dd,1H), δ=7.84 ppm (dd, 1H), δ=8.08 ppm (m,1H), pyridyl 5-H), δ=8.12 to 8.28 ppm (m,3H), δ=8.48 ppm (s,1H), δ=8.59 ppm (dd,1H), δ=8.88 ppm (d,1H); MS (M+H)+ 506.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with 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-48a55d9f8ee64f1b9b6c6b22936611dd
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

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