Water → 2-[2-(2-Propyn-1-yloxy)ethoxy]ethanamine

HRID 532085Notes

Reaction equation

HRID 532085 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][C:11]#[CH:12])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH2:10]([O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH2:1])[C:11]#[CH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 58078881HCID 58078881, compound

Product 1

HCID 552192912-[2-(2-Propyn-1-yloxy)ethoxy]ethanamineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-(2-azidoethoxy)ethoxy)prop-1-yne (s-4) (2 g, 11.82 mmol, 1.0 equiv) was dissolved in THF (30.5 mL). Triphenylphosphine (3.72 g, 14.20 mmol, 1.2 equiv.) and water (0.21 mL, 11.83 mol, 1.0 equiv.) were added to the solution and the reaction was allowed to stir at room temperature for 10 hours. The reaction was concentrated under reduced pressure and chromatographed (5% CH3OH in CHCl3, then 5% CH3OH in CHCl3+5% Et3N) to yield 2-(2-(prop-2-ynyloxy)ethoxy)ethanamine (s-5) as a pale green oil (1.35 g, 80%). IR (thin film) 3250 (m), 2863 (m), 2112 (w), 1589 (w), 1443 (w), 1349 (m), 1291 (w), 1093 (s), 1037 (m), 918 (w), 840 (w), 673 (m); 1H NMR (500 MHz, CDCl3) δ 4.21 (d, J=2.3 Hz, 2H), 3.73-3.68 (m, 2H), 3.68-3.62 (m, 2H), 3.51 (t, J=5.2 Hz, 2H), 2.87 (t, J=5.2 Hz, 2H), 2.43 (dd, J=2.4 Hz, 1H). 13C NMR (125 MHz, CDCl3) δ 79.7, 74.7, 73.7, 70.3, 69.2, 58.6, 41.9. HRMS (ES+) calc'd for C7H13NO2 (M+H) m/z 144.0980 Found 144.1019.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customchromatographed (5% CH3OH in CHCl3

Sources & evidence

ORD record
ord-efe47d9fd5234686b9464bb466962710
Source dataset
uspto-grants-2014_10
Patent number
US08852630B2

Reaction notes

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