Ethanol → HCID 49801329, compound

HRID 1187132Notes

Reaction equation

HRID 1187132 reaction equation
[BH4-].[Na+].C(O)C.[N:6]1([CH2:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:26])[CH2:11][CH2:10][N:9]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:14])[CH2:8][CH2:7]1>O>[N:6]1([CH2:24][CH:25]([C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)[OH:26])[CH2:11][CH2:10][N:9]([CH2:12][CH:13]([C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)[OH:14])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86647319HCID 86647319, compound

Product 1

HCID 49801329HCID 49801329, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaBH4 (308 mg, 8.15 mmol) was added to a 25 mL ethanol solution of 2,2′-piperazine-1,4-diylbis[1-(4-nitrophenyl)ethanone] (400 mg, 0.970 mmol) at 0° C. The reaction mixture was allowed to warm up to room temperature and stir overnight. The reaction mixture was poured into water and extracted twice with EtOAc. The combined organic layers were washed with brine twice, then dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by preparative TLC using 5% methanol in DCM to yield 2,2′-piperazine-1,4-diylbis[1-(4-nitrophenyl)ethanol].

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organic layers were washed with brine twice
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-7b38af987b604d519366b3969ece6a49
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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