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

HRID 419633Notes

Reaction equation

HRID 419633 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]3)[CH2:17][CH2:16]2)[CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[CH3:4]>C1COCC1.CO>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:25][CH2:26]3)[CH2:17][CH2:16]2)[CH:9]=[CH:10][C:11]=1[NH2:12])[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 594527701-{1-[3-(Ethyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine

Product 1

HCID 594529942-(Ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}anilineYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.41 g, 10.9 mmol) was added in portions to a stirring suspension of 1-{1-[3-(ethyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(methylsulfonyl)piperazine (1.50 g, 3.64 mmol) and NiCl2.6H2O (0.26 g, 1.1 mmol) in THF (15 mL) and MeOH (30 mL) at rt. The reaction mixture was allowed to stir at rt overnight 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 2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.40 g, 30%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.42-6.56 (m, 2H), 6.29 (dd, J=8.4, 2.3 Hz, 1H), 4.21 (br. s., 2H), 3.96 (q, J=6.9 Hz, 2H), 3.37-3.48 (m, 2H), 3.05-3.12 (m, 4H), 2.86 (s, 3H), 2.56-2.63 (m, 4H), 2.26-2.37 (m, 1H), 1.75-1.85 (m, 2H), 1.42-1.61 (m, 2H), 1.31 (t, J=7.0 Hz, 3H).

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-2086bdc6ef984b11ab20942d6febb3c5
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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