1,3-Propanediamine → 7-Octyn-1-ol

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.

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 (3×15 mL) and brine
6. dry with materialdried (MgSO4)
7. customEvaporation

ORD record

ord-abcb076a0ce4404db4518ad1d1b0ccf4

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05633258