n-{2-[3-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]ethyl}(phenylmethoxy)carboxamide → {2-[3-(2-Aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amine

HRID 48385Notes

Reaction equation

HRID 48385 reaction equation
[CH3:1][CH:2]([C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][NH:19]C(OCC2C=CC=CC=2)=O)[CH:14]=[CH:15][CH:16]=1)[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]>[Pd]>[NH2:19][CH2:18][CH2:17][C:13]1[CH:12]=[C:11]([CH:2]([CH3:1])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6])[CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 22743237n-{2-[3-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]ethyl}(phenylmethoxy)carboxamide

Product 1

HCID 22743247{2-[3-(2-Aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amineYield 100.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Scheme Va, step B: N-{2-[3-(1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]ethyl}(phenylmethoxy)carboxamide (0.84 g, 2 mmol) and 10% palladium on carbon (0.5 g, 60 mole %) were combined and hydrogenation was carried out in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, {2-[3-(2-aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amine, (0.57 g, 100%) as colorless oil. Electron spray M.S. 285 (M*+H).

Sources & evidence

ORD record
ord-e673e1f0e1f84e25952a1d3d6d9ded1b
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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