Sodium Hydroxide → 1-(1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

HRID 2424388Notes

Reaction equation

HRID 2424388 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 259188571-(3-Methoxy-4-nitrophenyl)piperidin-4-one

Product 1

HCID 567772491-(1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazineYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1-(3-Methoxy-4-nitro-phenyl)-piperidin-4-one (4.96 g, 0.020 mol) in dichloroethane (50 ml) is added N-methylpiperazine (2.7 ml, 0.024 mol) at 0° C. and the mixture is stirred at room temperature. After 4 h, sodium triacetoxy-borohydride (5.04 g, 0.024 mol) is added and the mixture is further stirred at room temperature for 24 h. After addition of 1N sodium hydroxide at 0° C., the mixture is poured into water and extracted three times with dichloromethane. The organic layer is combined and extracted three times with 1N hydrochloride. The water layer is basified with 2N sodium hydroxide and extracted three times with dichloromethane. The organic layer is washed with brine, dried over sodium sulfate, and evaporated in vacuo to give the title compound as yellow solids (6.04 g) in 91% yield.

Workup

  1. stirringthe mixture is further stirred at room temperature for 24 h
  2. extractionextracted three times with dichloromethane
  3. extractionextracted three times with 1N hydrochloride
  4. extractionextracted three times with dichloromethane
  5. washThe organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2ee775c677334758825795f915167fc3
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

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