1,3-Propanediamine → 7-Octyn-1-ol

HRID 1780779Notes

Reaction equation

HRID 1780779 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 and brine and dried (MgSO4). Evaporation gave a colorless oil which was used without further purification: 1H NMR (90 MHz, CDCl3) δ 3.65 (t, J=5 Hz, 2H, O--CH2), 2.23 (m, 2H, CH2), 2.0 (m, 1H, acetylenic), 1.7-1.2 (m, 8H, (CH2)4); IR (neat) nmax 3350, 2930, 2125 cm-1.

Workup

  1. temperatureThe flask was cooled to 0° C.
  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 and brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation
  8. customgave a colorless oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-de87afa26d714e14a6d512898b0c779c
Source dataset
uspto-grants-1997_05
Patent number
US05631262

Reaction notes

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