Sodium Hydroxide → 1-Amino-4-(2-thenoyl)piperazine

HRID 1655193Notes

Reaction equation

HRID 1655193 reaction equation
[N:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:15])[C:10]2[S:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)=O.[OH-].[Na+]>C(O)(=O)C.O.[Zn]>[NH2:1][N:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:15])[C:10]2[S:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 197912611-Nitroso-4-(2-thenoyl)piperazine

Product 1

HCID 197912671-Amino-4-(2-thenoyl)piperazineYield 70.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 1-nitroso-4-(2-thenoyl)piperazine (1.78 g) in a mixture of acetic acid (8 ml) and water (8 ml) was added Zn powder (1.55 g) in several portions at 6°-15° C. The suspension was stirred for 1.5 hours below 10° C. To the mixture was added acetic acid (4 ml) and Zn powder (780 mg) at 8°-12° C. The mixture was stirred for 2 hours at ambient temperature. To the suspension was added 17% aqueous sodium hydroxide solution (70 ml). The insoluble materials were filtered off. The aqueous layer was extracted with dichloromethane. The combined organic layers were dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution by 5% methanol in dichloromethane) to yield 1-amino-4-(2-thenoyl)piperazine (1.17 g) as a pale yellow syrup.

Workup

  1. stirringThe mixture was stirred for 2 hours at ambient temperature
  2. filtrationThe insoluble materials were filtered off
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. customThe combined organic layers were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (elution by 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e06b1f68e1a940cb97e3134035dfe7a7
Source dataset
uspto-grants-1993_10
Patent number
US05250528

Reaction notes

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