HCID 19385025, compound → N-[4-(2-aminoethyl)phenyl]Benzenesulfonamide

HRID 2399866Notes

Reaction equation

HRID 2399866 reaction equation
C1(COC([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:16][CH:15]=2)=O)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)(=[O:23])=[O:22])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 19385025HCID 19385025, compound

Product 1

HCID 15281645N-[4-(2-aminoethyl)phenyl]BenzenesulfonamideYield 89.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 600 mg (1.46 mmol) of Cbz amine from Example 5 in 18 mL of methanol was stirred over 20% palladium hydroxide on carbon under an atmosphere of hydrogen for 2.5 h. The reaction mixture was filtered through a Celite pad and concentrated to give 360 mg (89%) of a white solid: 1H NMR (400 MHz, CD3OD) δ7.73 (d, 2H, J=7.1 Hz), 7.52 (t, 1H, J=7.4 Hz), 7.44 (t, 2H, J=7.5 Hz), 7.04 (d, 2H, J=8.7 Hz), 6.99 (d, 2H, J=8.6 Hz), 2.82 (t, 2H, J=7.3 Hz), 2.66 (t, 2H, J=7.3 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3f3f9dd63a04411f992542672e48828d
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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