Ethanol → 2-[4-(4-Pyridinyl)piperazino]ethylamine

HRID 1663229Notes

Reaction equation

HRID 1663229 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(O)C.O.O.NN>C(OCC)C>[N:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 674365642-[2-(4-Pyridin-4-yl-piperazin-1-yl)-ethyl]-isoindole-1,3-dione

Product 1

HCID 184406752-[4-(4-Pyridinyl)piperazino]ethylamineYield 62.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 2-[2-(4-pyridin-4-yl-piperazin-1-yl)-ethyl]-isoindole-1,3-dione (1.52 g, 4.52 mmol), ethanol (47.5 mL), water (2.5 mL) and hydrazine hydrate (98%, 0.438 mL, 9.04 mmol) was refluxed for 3 h, then cooled and diluted with diethyl ether (100 mL). The precipitated crystals were filtered off, washed with diethyl ether and filtrate was concentrated. The residue was dissolved N sodium hydroxide (25 mL), extracted with dichloromethane (4×25 mL), the combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered and concentrated to yield 0.58 g (62%) of the title compound as a colorless oil.

Workup

  1. temperaturewas refluxed for 3 h
  2. temperaturecooled
  3. filtrationThe precipitated crystals were filtered off
  4. washwashed with diethyl ether and filtrate
  5. concentrationwas concentrated
  6. dissolutionThe residue was dissolved N sodium hydroxide (25 mL)
  7. extractionextracted with dichloromethane (4×25 mL)
  8. washthe combined organic layers were washed with brine (25 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-55f9490a13a146e2a0594283cc5b6c7b
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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