Sodium borohydride → 5-Methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline

HRID 419649Notes

Reaction equation

HRID 419649 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1>C1COCC1.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:3][C:4]1[C:5]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:25][CH2:26]3)[CH2:17][CH2:16]2)=[CH:6][C:7]([O:13][CH3:14])=[C:8]([CH:9]=1)[NH2:10]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 59452972HCID 59452972, compound

Product 1

HCID 594526035-Methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}anilineYield 57.4%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.30 g, 7.93 mmol) was added in portions to a stirring suspension of 1-{1-[2-methyl-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (1.09 g, 2.64 mmol) and Nickel(II)chloride hexahydrate (0.19 g, 0.8 mmol) in THF (10 mL) and MeOH (20 mL) at rt. The reaction mixture was allowed to stir at rt for 2 h and then it was concentrated in vacuo. The residue was taken up in DCM and passed through a bed of celite. The resultant filtrate was then concentrated onto silica gel and purified by flash chromatography to afford 5-methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.58 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.55 (s, 1H), 6.43 (s, 1H), 4.30 (s, 2H), 3.70 (s, 3H), 3.05-3.15 (m, 4H), 2.89-2.96 (m, 2H), 2.86 (s, 3H), 2.52-2.65 (m, 6H), 2.26-2.41 (m, 1H), 2.06 (s, 3H), 1.74-1.85 (m, 2H), 1.43-1.63 (m, 2H).

Workup

  1. concentrationit was concentrated in vacuo
  2. concentrationThe resultant filtrate was then concentrated onto silica gel
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-953b4dc7bc28437b8abaf331e947f3cf
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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