Acetic Acid → N-[4-(5-Dimethylamino-pentyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

HRID 1841611Notes

Reaction equation

HRID 1841611 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH3:28])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:10][CH:9]=1.CC(O)=O>CO.[Pd]>[CH3:29][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]([CH3:28])[S:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 23446642N-[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 23446494N-[4-(5-Dimethylamino-pentyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamideYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 40 mg (0.094 mmol) of N-[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide in 3 ml MeOH/0.3 ml dioxane was treated with 0.094 ml 1N AcOH in MeOH followed by 4 mg Pd/C10%, type EION (under argon) and then hydrogenated (1 atm) for 3 h. The reaction mixture was filtered (Celite) and extracted with aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution, dried (Na2SO4) and evaporated to yield 27 mg (66%) of N-[4-(5-Dimethylamino-pentyl)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 429 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered (Celite)
  2. extractionextracted with aqueous sat. NaHCO3/Et2O (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a2a33d95802940b4aa80d47e95467e4f
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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