1,3-Propanediamine → 7-Octyn-1-ol

HRID 1780775Notes

Reaction equation

HRID 1780775 reaction equation
NCCCN.[CH2:6]([OH:14])[CH2:7][C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13]>CCCCCC>[CH2:6]([OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 846943-Octyn-1-ol

Product 1

HCID 701007-Octyn-1-ol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

35% KH in mineral oil (27 g, 240 mmol) under an argon atmosphere was washed with hexane and treated dropwise with 1,3-diaminopropane. The mixture was stirred at room temperature until it became homogeneous. The flask was cooled to 0∞C and 3-octyn-1-ol (10 g, 79 mmol, Lancaster Synthesis) was slowly added. The reaction was then stirred at room temperature for 18 hours. The reaction was quenched with H2O (50 mL) and the product was extracted into ether. The organic layer was washed with 10% HCl (3×15 mL) and brine and dried (MgSO4). Evaporation gave the title product which was used without further purification: 1H NMR (90 MHz, CDCl3) d 3.65 (t, J=5 Hz, 2H, OCH2), 2.23 (m, 2H, CH2), 2.0 (m, 1H, acetylenic), 1.7-1.2 (m, 8H, (CH2)4); IR (neat) umax 3350, 2930, 2125 cm-1.

Workup

  1. additionwas slowly added
  2. stirringThe reaction was then stirred at room temperature for 18 hours
  3. customThe reaction was quenched with H2O (50 mL)
  4. extractionthe product was extracted into ether
  5. washThe organic layer was washed with 10% HCl (3×15 mL) and brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation

Sources & evidence

ORD record
ord-530fd71ea9dc478c961cb83e7425e289
Source dataset
uspto-grants-1997_05
Patent number
US05631262

Reaction notes

Loading…