Triphenylphosphine → 1-(3-Methylpyridin-2-yl)ethan-1-amine

HRID 251204Notes

Reaction equation

HRID 251204 reaction equation
[N:1]([CH:4]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:5])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH3:12][C:11]1[C:6]([CH:4]([NH2:1])[CH3:5])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 914713542-(1-Azido-ethyl)-3-methyl-pyridine

Product 1

HCID 457911661-(3-Methylpyridin-2-yl)ethan-1-amineYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the above azide (254 mg, 1.57 mmol) and PPh3 (828 mg, 3.16 mmol) in 10% aqueous THF (10 mL) was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica (CH2Cl2/MeOH, 9:1), giving 1-(3-methyl-pyridin-2-yl)-ethylamine as a yellow liquid (163 mg, 1.20 mmol, 76%). 1H NMR (CDCl3) δ 1.35 (d, 3H, J=6.6 Hz), 2.00 (s, 2H), 2.33 (s, 3H), 4.30 (q, 1H, J=6.6 Hz), 7.05 (dd, 1H, J=7.5, 4.8 Hz), 7.40 (d, 1H, J=7.5 Hz), 8.41 (d, 1H, J=4.2 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica (CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record
ord-a3eaf16692a04a948bffd7058437286f
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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