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

HRID 1592617Notes

Reaction equation

HRID 1592617 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-42f4fc2f483f43a8a59379c75068d1df
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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