Tetrahydrofuran → 4-Ethylpiperazin-1-amine

HRID 2286504Notes

Reaction equation

HRID 2286504 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([N:9]=O)[CH2:5][CH2:4]1)[CH3:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[NH2:9][N:6]1[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 125546241-Ethyl-4-nitrosopiperazineHCID 21226445Aluminium lithium hydride

Product 1

HCID 30157254-Ethylpiperazin-1-amineYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of N-ethyl-N'-nitroso piperazine (4.0 g, 0.028 mole) in anhydrous freshly distilled tetrahydrofuran (80 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (1.5 g, excess) under nitrogen in anhydrous tetahydrofuran (160 ml) at 20°-25° C. After addition stirring was continued for a further 8 hours. Work up via controlled addition of water (1.5 ml), 10% sodium hydroxide (2.25 ml) and water (3.75 ml) gave N-amino-N'-ethyl piperazine (2.26 g, 63%) as a pale straw coloured oil.

Workup

  1. additionAfter addition

Sources & evidence

ORD record
ord-d9ac563f6dc0488fbae0caca4e5d0063
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

Loading…