Methanol → 2-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

HRID 419644Notes

Reaction equation

HRID 419644 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.CO.[BH4-].[Na+]>C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydride2×HCID 598602551-(3-Methoxy-4-nitro-phenyl)-4-methylsulfonyl-piperazine

Product 1

HCID 598602722-(Methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-[3-(Methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)piperazine (1.09 g, 3.46 mmol) was suspended in 5 mL THF and 10 mL MeOH in a 100 mL round bottom flask. Nickle(II)chloride hexahydrate (0.247 g, 1.04 mmol) was added followed by slow addition of NaBH4 (0.392 g, 10.38 mmol). TLC analysis indicated reaction complete after addition of NaBH4. Reaction mixture was adsorbed on SiO2 and purified via column chromatography using a gradient of 0-10% MeOH in DCM. Fractions were combined and rotovapped to give the title compound of step B. (0.925 g, 3.24 mmol, 93%); MS (ESI): 285 [M+H]+.

Workup

  1. customreaction
  2. customReaction mixture
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-93280bf8391f478da0bd341a2fbbe156
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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