Triethylamine → N-(2-azidoethyl)tetradecanamide

HRID 529916Notes

Reaction equation

HRID 529916 reaction equation
[N:1]([CH2:4][CH2:5][NH2:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[C:14](Cl)(=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[N:1]([CH2:4][CH2:5][NH:6][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 66986Myristoyl chloride

Product 1

HCID 57914356N-(2-azidoethyl)tetradecanamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL round-bottomed flask equipped with a magnetic stir bar was added 2-azidoethanamine (0.102 g, 1.18 mmol), DCM (5 mL) and then triethylamine (0.239 g, 2.37 mmol). To this reaction mixture, tetradecanoyl chloride (0.292 g, 1.18 mmol) was added dropwise and allowed to stir at room temperature for 24 hr. Then, the reaction mixture was concentrated de vacuo and then purified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane) to give N-(2-azidoethyl)tetradecanamide (0.245 g, 79% yield). 1H NMR (300 MHz, CDCl3) δ 5.86 (s, 1H), δ 3.42 (s, 41-1), δ 2.18 (t, J=7.8 Hz, 2H), δ 1.62 (m, 2H), δ 1.24 (m, 20H), δ 0.87 (t, J=3.9 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3) δ 173.7, 51.2, 39.1, 36.9, 32.1, 29.9, 29.8, 29.7, 29.6, 29.5, 25.9, 22.9, 14.4 ppm; HRMS (ESI) calcd for C16H32N4O (M+) 296.2576. found 296.2566.

Workup

  1. customTo a 25 mL round-bottomed flask equipped with a magnetic stir bar
  2. concentrationThen, the reaction mixture was concentrated de vacuo
  3. custompurified via silica gel column chromatography (100% dichloromethane to 1:40 methanol:dichloromethane)

Sources & evidence

ORD record
ord-c0899e8c17eb41049da4cadf64a48aab
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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