n-{2-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]ethyl}(phenylmethoxy)carboxamide → {2-[4-(2-Aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amine

HRID 48379Notes

Reaction equation

HRID 48379 reaction equation
[CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19]C(OCC2C=CC=CC=2)=O)=[CH:13][CH:12]=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:14]1[CH:13]=[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]=1

Participants

3

Reactant 1

HCID 22743233n-{2-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]ethyl}(phenylmethoxy)carboxamide

Product 1

HCID 22743208{2-[4-(2-Aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amineYield 37%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Scheme Va, step B: N-{2-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]ethyl}(phenylmethoxy)carboxamide (0.6 g, 1.44 mmol) and 10% palladium on carbon (0.5 g, 35 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-[4-(2-aminoethyl)phenyl]propyl}[(methylethyl)sulfonyl]amine, (0.15 g, 37%) as colorless oil. Electron spray M.S. 285 (M*+H).

Sources & evidence

ORD record
ord-dbade94c65af41eca908b83196626da2
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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