Triethylamine → 2-Chloro-4-(4-methoxypiperidinosulphonyl)benzene sulphonamide

HRID 1282997Notes

Reaction equation

HRID 1282997 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[Cl:16][C:17]1[CH:18]=[C:19]([S:27](Cl)(=[O:29])=[O:28])[CH:20]=[CH:21][C:22]=1[S:23](=[O:26])(=[O:25])[NH2:24]>CC(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([S:27]([N:13]2[CH2:14][CH2:15][CH:10]([O:9][CH3:8])[CH2:11][CH2:12]2)(=[O:28])=[O:29])[CH:20]=[CH:21][C:22]=1[S:23]([NH2:24])(=[O:25])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 776664-MethoxypiperidineHCID 130527963-Chloro-4-sulfamoylbenzene-1-sulfonyl chloride

Product 1

HCID 159428252-Chloro-4-(4-methoxypiperidinosulphonyl)benzene sulphonamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Triethylamine (4.2 ml) and 4-methoxypiperidine (3.15 g) were added to a solution of 3-chloro-4-sulphamoyl-benzene sulphonyl chloride (8.7 g) in acetone (100 ml). The mixture was stirred at room temperature for 1 hour and then poured into 50 ml of N-hydrochloric acid. The resulting product was removed by filtration, washed with water and recrystallized from isopropanol to give the desired compound (8.4 g), m.p. 165°-167°C.

Workup

  1. customThe resulting product was removed by filtration
  2. washwashed with water
  3. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-717f082f5bc2480488a7785c9e240df3
Source dataset
uspto-grants-1976_08
Patent number
US03974155

Reaction notes

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