1,3-Propanediamine → Pentadec-14-yn-1-ol

HRID 398221Notes

Reaction equation

HRID 398221 reaction equation
C(O)CCCCCCC#C.[CH2:11]([OH:26])[C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].NCCCN>>[CH2:11]([OH:26])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25]

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 5344292-Pentadecyn-1-olHCID 38061428-Nonyn-1-ol

Product 1

HCID 10977125Pentadec-14-yn-1-ol

Procedure

The same procedure for 8-nonyn-1-ol was followed with 2- pentadecyn-1-ol (4.51 g, 20.1 mmol), KH (2.38 g, 59.4 mmol), and 1,3-diaminopropane (65 mL). This produced 3.18 g of white solid (70%): mp 42-44° C. IR (thin film( ν 3430, 2926, 2252 cm−1: 1H—NMR δ4.30 (t, 1H, J=5.0 Hz), 3.64 (t, 2H, J=6.6 Hz), 2.18 (td, 2H, J=2.6 Hz, 6.6 Hz), 1.94 (t, 1H, J=2.6 Hz), 1.49-1.26 (bm, 22H); 13C—NMR δ 84.8, 68.0, 63.1, 32.8, 29.6, (2C), 29.5 (2C), 29.4, 28.9, 28.5, 28.7, 28.0, 25.7, 18.4; MS m/z 231.53 (M++Li). Anal. Calcd for C15H28O: C, 80.29; H, 12.58. Found: C, 18.20; H, 12.50.

Sources & evidence

ORD record
ord-c1e9a808ec194f0d9f62828fb0d6062c
Source dataset
uspto-grants-2003_08
Patent number
US06610835B1

Reaction notes

Loading…