Sodium borohydride → (2-(Ethyloxy)-4-[4-(1-methylethyl)-1-piperazinyl]phenyl}amine

HRID 419542Notes

Reaction equation

HRID 419542 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2].[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO.C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:14][CH2:15][N:16]([CH:19]([CH3:21])[CH3:20])[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[NH2:10])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 594529251-[3-(Ethyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine

Product 1

HCID 59452785(2-(Ethyloxy)-4-[4-(1-methylethyl)-1-piperazinyl]phenyl}amineYield 93%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 1-[3-(ethyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine (0.285 g, 0.97 mmol) and nickel(II) chloride hexahydrate (0.116 g, 0.48 mmol) was stirred in 2:1 MeOH/THF (10 mL) under N2 at rt. To this mixture was added NaBH4 (0.129 g, 3.4 mmol) in 2 equal portions over 5 min. The reaction was stirred at rt for about 45 min, then concentrated under vacuum. The residue was dissolved in DCM and poured through Celite, washing with DCM and EtOAc. The filtrate was concentrated and chromatographed on silica gel to give the title compound of step B (238 mg, 0.90 mmol, 93%) as a grey oil. MS (ESI): 264 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in DCM
  3. additionpoured through Celite
  4. washwashing with DCM and EtOAc
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-57603de864ea42a09709ce1157cdd1bd
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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