Ethanol → 2-[(Phenylsulfonyl)methyl]-6-(4-methylpiperazin-1-yl)-pyridin-3-ylamine

HRID 2102772Notes

Reaction equation

HRID 2102772 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([CH2:17][S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[N:9]=2)[CH2:4][CH2:3]1.C(O)C>[Pd].C1COCC1>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[N:9]=[C:10]([CH2:17][S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:20])=[O:19])[C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 702EthanolHCID 589340691-Methyl-4-{5-nitro-6-[(phenylsulfonyl)methyl]pyridin-2-yl}piperazine

Product 1

HCID 589340632-[(Phenylsulfonyl)methyl]-6-(4-methylpiperazin-1-yl)-pyridin-3-ylamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-methyl-4-{5-nitro-6-[(phenylsulfonyl)methyl]pyridin-2-yl}-piperazine (1.60 g, 4.35 mmol) and 10% Pd/C (200 mg) in a 1:1 mixture of ethanol:THF is hydrogenated at 45 psi for 4 h at ambient temperatures. The catalyst is filtered off and the filtrate is concentrated in vacuo to afford the title compound as a yellow solid, 1.45 g (99% yield), identified by NMR analysis.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3bf515f18cae4ee98fdd5c9e914befda
Source dataset
uspto-grants-2009_08
Patent number
US07576087B2

Reaction notes

Loading…