Hydrazine hydrate (1:1) → 2-[(6-Dimethylaminomethyl-2-pyridyl)methylthio]ethylamine

HRID 1154698Notes

Reaction equation

HRID 1154698 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:10]=[C:9]([CH2:11][S:12][CH2:13][CH2:14][N:15]2C(=O)C3=CC=CC=C3C2=O)[CH:8]=[CH:7][CH:6]=1)[CH3:3].O.NN>CO>[NH2:15][CH2:14][CH2:13][S:12][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[N:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 204342816-Dimethylaminomethyl-2-[(2-phthalimidoethyl)thiomethyl]pyridine

Product 1

HCID 212920152-[(6-Dimethylaminomethyl-2-pyridyl)methylthio]ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Dimethylaminomethyl-2-[(2-phthalimidoethyl) thiomethyl]pyridine (24.3 g, 0.068 mol) is dissolved in methanol (150 ml) and hydrazine hydrate (4.8 g, 0.087 mol) is added. The solution is refluxed for 11/2 hours and is concentrated in vacuo. The solid residue is dissolved in water (250 ml) 12N HCl (35 ml) is added and the mixture is cooled and filtered. The filtrate is washed with chloroform and concentrated in vacuo. The residue is basified with excess sodium bicarbonate and concentrated to dryness in vacuo. The solid residue is extracted with chloroform/methanol (50/50) (200 ml) and the extract is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 10.3 g of 2-[(2-aminoethyl)thiomethyl]-6-dimethylaminomethyl pyridine as a light amber oil.

Workup

  1. temperatureThe solution is refluxed for 11/2 hours
  2. concentrationis concentrated in vacuo
  3. dissolutionThe solid residue is dissolved in water (250 ml) 12N HCl (35 ml)
  4. additionis added
  5. temperaturethe mixture is cooled
  6. filtrationfiltered
  7. washThe filtrate is washed with chloroform
  8. concentrationconcentrated in vacuo
  9. concentrationconcentrated to dryness in vacuo
  10. extractionThe solid residue is extracted with chloroform/methanol (50/50) (200 ml)
  11. dry with materialthe extract is dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd27be840a7d49248bbbb11d2d98c79c
Source dataset
uspto-grants-1984_12
Patent number
US04490533

Reaction notes

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