Water → 1-(4-Nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanol

HRID 1187130Notes

Reaction equation

HRID 1187130 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:31])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].O>C(O)C>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([OH:31])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)[CH2:16][CH2:15]2)=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 498013261-(4-Nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanone

Product 1

HCID 498013271-(4-Nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (8.0 mg, 0.21 mmol) was added to 1-(4-nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanone (20 mg, 0.050 mmol) in ethanol (1 mL) and stirred at RT for 2 h. The reaction mixture was poured into water and extracted twice with EtOAc, twice with brine, then was dried over MgSO4, and evaporated to dryness. The crude material was purified by preparative TLC using 5% (10% NH4OH in MeOH): 95% DCM solvent system to yield 1-(4-nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanol.

Workup

  1. extractionextracted twice with EtOAc, twice with brine
  2. dry with materialwas dried over MgSO4
  3. customevaporated to dryness
  4. customThe crude material was purified by preparative TLC

Sources & evidence

ORD record
ord-9dd749448f8e4f1ca89c3d695984c401
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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