4-Chlorobenzenesulfonyl chloride → HCID 69146664, compound

HRID 2223905Notes

Reaction equation

HRID 2223905 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:20])[CH2:14][CH2:13]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.N12CCN(CC1)CC2.[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=1>ClCCl.C(Cl)(Cl)Cl>[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([S:48]([NH:1][CH2:2][CH2:3][C:4]2([CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH:15]([N:18]([C:26]4[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=4)[C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)=[O:20])[CH2:14][CH2:13]3)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)(=[O:50])=[O:49])=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 9237DabcoHCID 23109894HCID 23109894, compound

Product 1

HCID 69146664HCID 69146664, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-[2-[1-(2-aminoethyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (synthesized in Example 18) (199 mg) in dichloromethane (3 mL) were added 1,4-diazabicyclo[2.2.2]octane (100 mg) and p-chlorobenzenesulfonyl chloride (100 mg) successively. The solution was stirred at room temperature for 2 hours. The reaction solution was diluted with chloroform, washed in turn with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3)] to give the title compound (181 mg).

Workup

  1. washwashed in turn with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (7:3)]

Sources & evidence

ORD record
ord-3a0cb6c1827e45f693c66d2ea93240ef
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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