Hydrochloric Acid → n-(4-Hydroxy-benzyl)-4-methoxy-n-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide hydrochloride salt

HRID 1827529Notes

Reaction equation

HRID 1827529 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:29][CH:28]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C3CCCCO3)=[CH:16][CH:15]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[ClH:41].O1CCOCC1>C(O)C>[ClH:41].[OH:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:12]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:29][CH:28]=2)[S:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)(=[O:10])=[O:11])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 221374154-methoxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide

Product 1

HCID 22137428n-(4-Hydroxy-benzyl)-4-methoxy-n-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide hydrochloride salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methoxy-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-benzenesulfonamide (1.58 g, 2.79 mmol) was suspended in 3:1 ethanol:1N HCl (30 mL) and the solution was stirred at room temperature for 24 hr. The reaction mixture was quenched with sodium bicarbonate solution and the aqueous solution was washed with methylene chloride. The organic layer was dried (sodium sulfate), filtered, and concentrated to a white solid. The crude material was purified via Biotage® (A Dynax Corp., Charlottesville, Va.) chromatography using 10% methanol/methylene chloride as the eluant. The purified material was suspended in methanol (15 mL) and 4.0M HCl in dioxane (1.5 equiv.) was added. The mixture was stirred at room temperature and was concentrated to dryness to yield the title compound as the HCl salt. MS 483.1 (M+1)+

Workup

  1. customThe reaction mixture was quenched with sodium bicarbonate solution
  2. washthe aqueous solution was washed with methylene chloride
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid
  6. customThe crude material was purified via Biotage® (A Dynax Corp
  7. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-22fe8efdbc824a46a5f9a5ef79018f51
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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