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

HRID 1827532Notes

Reaction equation

HRID 1827532 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C3CCCCO3)=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.O>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)=[CH:30][CH:31]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 221372724-hydroxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

Product 1

HCID 221373084-Hydroxy-N-(4-hydroxy-benzyl)-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide in methanol (20 mL) was added 1N HCl (5 mL). After stirring for 2 hr., water was added and the aqueous solution was washed with methylene chloride (3×). The combined organic solutions were washed with saturated aqueous sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated. The residue was purified via radial chromatography using a solvent gradient (methylene chloride to 10% methanol/methylene chloride) to provide the title compound. 1H NMR (CD3OD) δ 7.44 (d, 2H, J=8.0 Hz), 6.96 (d, 2H, J=8.0 Hz), 6.85–6.74 (m, 4H), 6.73 (d, 2H, J=8.0 Hz), 6.58 (d, 2H, J=8.0 Hz), 4.55 (s, 2H), 4.02 (t, 2H, J=5.6 Hz), 2.89 (t, 2H, J=5.6 Hz), 2.67 (bs, 4H), 1.81 (bs, 4H).

Workup

  1. washthe aqueous solution was washed with methylene chloride (3×)
  2. washThe combined organic solutions were washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via radial chromatography

Sources & evidence

ORD record
ord-15a21f5a88534f90a032271c2e91fc2a
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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