Hydrochloric Acid → 4-Isopropyl-N-(3-pyrrolidin-3-yl-phenyl)-benzenesulfonamide

HRID 1260228Notes

Reaction equation

HRID 1260228 reaction equation
COC([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:11]=2)[CH2:6]1)=O.Cl>CCO>[CH:26]([C:23]1[CH:24]=[CH:25][C:20]([S:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH:7]3[CH2:8][CH2:9][NH:5][CH2:6]3)[CH:11]=2)(=[O:18])=[O:19])=[CH:21][CH:22]=1)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 536286573-[3-(4-Isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester

Product 1

HCID 574700764-Isopropyl-N-(3-pyrrolidin-3-yl-phenyl)-benzenesulfonamideYield 25.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[3-(4-Isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester (900 mg, 1.13 mmol) and HCl (8M, 273.90 mmol) in EtOH (20 ml) were heated to reflux for 48 h. The mixture was extracted twice with ethyl acetate and then NaOH (2M) was added. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated sodium chloride solution, dried over MgSO4 and evaporated under reduced pressure to give the product as a brown oil (100 mg, 13%).

Workup

  1. temperatureto reflux for 48 h
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. additionNaOH (2M) was added
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with water and saturated sodium chloride solution
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-da0f5195064d4726a79f8613219e4507
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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