Hydrochloric Acid → 2-Chloro-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide

HRID 1827534Notes

Reaction equation

HRID 1827534 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:32][CH:31]=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23]C2CCCCO2)=[CH:19][CH:18]=1)(=[O:14])=[O:13].Cl>C(O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:34][CH:35]=1)(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221373332-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 221374712-Chloro-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-4-trifluoromethyl-benzenesulfonamideYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of crude 2-chloro-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-4-trifluoromethyl-benzenesulfonamide (0.096 g, 0.15 mmol) in 4 mL ethanol was added 1 mL of 1.2N HCl. The reaction mixture was stirred at room temperature for 24 hr. and was diluted with 10 mL saturated aqueous sodium bicarbonate. The aqueous solution was washed with methylene chloride (2×10 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 10% methanol/methylene chloride) to afford 0.039 g (84%) of the title compound. MS 555.3 (M+1)+

Workup

  1. washThe aqueous solution was washed with methylene chloride (2×10 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-13516c9c7e8d405a8b392c4e49b239a8
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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