(4-Aminomethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine → 4-(Aminomethyl)pyridin-2-amine

HRID 887635Notes

Reaction equation

HRID 887635 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9]CC2C=CC(OC)=CC=2)[CH:4]=1>C(O)(C(F)(F)F)=O>[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1

Participants

3

Reactant 1

HCID 21961478(4-Aminomethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine

Product 1

HCID 341768864-(Aminomethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(4-Aminomethyl-pyridin-2-yl)-(4-methoxy-benzyl)-amine (12 g, 50 mmole) was dissolved in TFA (150 mL) and heated to reflux for 1 h. After cooling, the reaction mixture was concentrated in vacuum and the residue was partitioned between HCl (1N, aq.) and EtOAc. The aqueous layer was washed with EtOAc then hexanes and concentrated to dryness in vacuum to give an off white solid as a dihydrochloric salt.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated in vacuum
  5. customthe residue was partitioned between HCl (1N, aq.) and EtOAc
  6. washThe aqueous layer was washed with EtOAc
  7. concentrationhexanes and concentrated to dryness in vacuum
  8. customto give an off white solid as a dihydrochloric salt

Sources & evidence

ORD record
ord-dd5444b698f64eae8e35c443411a4c67
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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