Sodium Hydroxide → 1-[2-Fluoro-2-(4-nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine

HRID 1474388Notes

Reaction equation

HRID 1474388 reaction equation
CCN(S(F)(F)[F:7])CC.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19](O)[CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[CH2:23][CH2:22]2)=[CH:15][CH:14]=1)([O-:12])=[O:11].[OH-].[Na+]>C(Cl)Cl>[F:7][CH:19]([C:16]1[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=1)[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 123472(Diethylamino)sulfur trifluorideHCID 498013271-(4-Nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanol

Product 1

HCID 498013281-[2-Fluoro-2-(4-nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (6.6 μL, 0.050 mmol) was added to 1-(4-nitrophenyl)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethanol (10 mg, 0.025 mmol) in DCM (1 mL) and the resulting mixture was stirred at RT for 72 h. Then 1 N NaOH was added and the mixture was extracted twice with DCM. The combined organic layers were dried over MgSO4, filtered, and evaporated to dryness. The crude product was purified by mass directed preparative HPLC to yield 1-[2-fluoro-2-(4-nitrophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine.

Workup

  1. extractionthe mixture was extracted twice with DCM
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by mass

Sources & evidence

ORD record
ord-3b24d35659024a82b9a665034aeb0c7f
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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