Water → N-amino-N'-2-thenylpiperazine

HRID 2286508Notes

Reaction equation

HRID 2286508 reaction equation
[N:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[S:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:1][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[S:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23461669N-nitroso-N'-2-thenylpiperazine

Product 1

HCID 23461656N-amino-N'-2-thenylpiperazineYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-nitroso-N'-2-thenylpiperazine (3.0 g, 0.014 mole) in anhydrous freshly distilled tetrahydrofurane (30 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (1.5 g excess) under nitrogen in anhydrous tetrahydrofuran (150 ml) at 60°-65° C. After addition, stirring was continued for 3 hours. Work-up via cooling, controlled addition of water (1.5 ml), 10% sodium hydroxide (2.25 ml) and water (3.75 ml) followed by filtration, drying over potassium carbonate, filtration and evaporation in vacuo gave N-amino-N'-2-thenyl-piperazine (2.7 g, 96%) as an almost colourless oil, used without further purification,

Workup

  1. additionAfter addition
  2. temperatureWork-up via cooling
  3. filtrationfollowed by filtration
  4. dry with materialdrying over potassium carbonate, filtration and evaporation in vacuo

Sources & evidence

ORD record
ord-f6fd110077b54ec0a75dd8e66d69e5e2
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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