Hydrochloric Acid → HCID 22137273, compound

HRID 1827563Notes

Reaction equation

HRID 1827563 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([N:13]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:31][CH:30]=1)[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C2CCCCO2)=[CH:18][CH:17]=1)[CH3:15])(=[O:12])=[O:11].Cl>C(O)C.C(=O)(O)[O-].[Na+]>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([CH:14]([N:13]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]3[CH2:39][CH2:40][CH2:41][CH2:42]3)=[CH:31][CH:30]=2)[S:10]([C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])(=[O:12])=[O:11])[CH3:15])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22137401HCID 22137401, compound

Product 1

HCID 22137273HCID 22137273, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of crude 2,4,6-trimethyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-N-{1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethyl}-benzenesulfonamide (0.071 g, 0.12 mmol) in 4 mL absolute ethanol was added 0.8 mL of 1.2N HCl. The reaction mixture was stirred at room temperature overnight, was diluted with 10 mL saturated aqueous sodium bicarbonate, and the aqueous solution was washed with methylene chloride (3×10 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated. The residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 15% methanol/methylene chloride) to afford 0.010 g of N-[1-(4-hydroxy-phenyl)-ethyl]-2,4,6-trimethyl-N-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzenesulfonamide. MS 509.0 (M+1)+

Workup

  1. washthe aqueous solution was washed with methylene chloride (3×10 mL)
  2. dry with materialThe combined organic layers were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (1.0 mm silica gel layer, elution with 15% methanol/methylene chloride)

Sources & evidence

ORD record
ord-ceaac0806a4c46b99dc2fa88e3f763d8
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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