n-{3-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]propyl}(phenylmethoxy)carboxamide → {2-[4-(3-Aminopropyl)phenyl]propyl}[(methylethyl)sulfonyl]amine

HRID 48375Notes

Reaction equation

HRID 48375 reaction equation
[CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][NH:20]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]>[NH2:20][CH2:19][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 22743262n-{3-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]propyl}(phenylmethoxy)carboxamide

Product 1

HCID 22743228{2-[4-(3-Aminopropyl)phenyl]propyl}[(methylethyl)sulfonyl]amineYield 116%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Scheme Vc, step B: N-{3-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]propyl}(phenylmethoxy)carboxamide (1 g, 2.31 mmol) and 10% palladium on carbon (0.5 g, 25 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-(3-aminopropyl)phenyl]propyl}[(methylethyl)sulfonyl]amine, (0.8 g, 87%) as a colorless oil. Electron spray M.S. 299 (M*+H).

Sources & evidence

ORD record
ord-1b09e14a8e974336ab461e2be0139622
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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