(1-Methanesulfonyl-piperidin-4-ylmethyl)-(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine → N-(1-methanesulfonyl-piperidin-4-ylmethyl)-N-propyl-1,2,3,4-tetrahydro-naphthalene-2,7-diamine

HRID 983469Notes

Reaction equation

HRID 983469 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]([CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([N+:26]([O-])=O)=[CH:21][CH:22]=3)[CH2:17]2)[CH2:13][CH2:14][CH3:15])[CH2:7][CH2:6]1)(=[O:4])=[O:3]>C(O)C.[Pd]>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]([CH2:13][CH2:14][CH3:15])[CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([NH2:26])=[CH:21][CH:22]=3)[CH2:17]2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 21362804(1-Methanesulfonyl-piperidin-4-ylmethyl)-(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine

Product 1

HCID 21362805N-(1-methanesulfonyl-piperidin-4-ylmethyl)-N-propyl-1,2,3,4-tetrahydro-naphthalene-2,7-diamineYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1-methanesulfonyl-piperidin-4-ylmethyl)-(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine (490 mg, 1.20 mmol) in ethanol (30 mL) was added 10% palladium on charcoal (50 mg). The solution was shaken on a Parr shaker for 24 h at 55 psi of H2. The solution was filtered through Celite® and concentrated to afford N-(1-methanesulfonyl-piperidin-4-ylmethyl)-N-propyl-1,2,3,4-tetrahydro-naphthalene-2,7-diamine (400 mg) 85, [M+H]+=380, which was used directly in the next step.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-40784994371042fd8e0e5810c51dde2a
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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