1,12-Dodecanediamine → N-(12-Aminododecyl)-4-hydroxy-4-ethyl-hexanamide

HRID 595383

Reaction equation

HRID 595383 reaction equation
[CH2:1]([C:3]1([CH2:9][CH3:10])[O:8][C:6](=[O:7])[CH2:5][CH2:4]1)[CH3:2].[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24]>O>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:6](=[O:7])[CH2:5][CH2:4][C:3]([OH:8])([CH2:9][CH3:10])[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 177271,12-DodecanediamineHCID 2525615,5-Diethyldihydrofuran-2(3h)-one

Product 1

HCID 86692177N-(12-Aminododecyl)-4-hydroxy-4-ethyl-hexanamideYield 30.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A procedure reported previously by us was followed. γ,γ-Diethyl-γ-butyrolactone (2.7 g, 19.1 mmol, 1.0 eq), 1,12-diaminododecane (9.6 g, 47.7 mmol, 2.5 eq), and water (8.0 mL) were combined. The solution was refluxed under a nitrogen atmosphere overnight. A yellow solution was formed. After cooling to room temperature, water was removed under reduced pressure. The yellow oily residue was purified by flash column chromatography (SiO2, Et2O/CH3OH/CH3CN/Et3N=5:2:2:1) to give 6 as a light yellow solid (2.0 g, 30%): Rf=0.5 (SiO2, Et2O/CH3OH/CH3CN/Et3N=5:2:2:1); 1H NMR (400 MHz, CDCl3) δ 5.67 (br s, 1H), 3.20 (q, 4H, J=7.2 Hz), 2.67 (t, 2H, J=7.2 Hz), 2.25 (t, 2H, J=7.2 Hz), 2.02 (br s, 3H), 1.74 (t, 2H, J=7.2 Hz), 1.50-1.40 (m, 8H), 1.33-1.20 (m, 16H), 0.84 (t, 6H, J=7.6 Hz); 13C NMR (100 MHz, CDCl3) δ 174.2, 73.9, 42.2, 39.9, 33.7, 31.0, 30.9, 29.73, 29.69, 29.4, 27.1, 27.0, 8.1; HRMS (ESI) m/z calcd for C20H43N2O2 [M+H]+ 343.3325. found 343.3321.

Workup

  1. temperatureThe solution was refluxed under a nitrogen atmosphere overnight
  2. customA yellow solution was formed
  3. customwater was removed under reduced pressure
  4. customThe yellow oily residue was purified by flash column chromatography (SiO2, Et2O/CH3OH/CH3CN/Et3N=5:2:2:1)

Sources & evidence

ORD record
ord-9d7e8144a0ea476a9b66e64a0fdbfd36
Source dataset
uspto-grants-2016_01
Patent number
US09243023B2

Linked notes

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