Tripropargylamine → 4-(Dodecyloxy)benzyltripropargylammonium bromide

HRID 1629581Notes

Reaction equation

HRID 1629581 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]#[CH:10])[CH2:5][C:6]#[CH:7])[C:2]#[CH:3].[CH2:11]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][Br:29])=[CH:26][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CC(C)=O>[Br-:29].[CH2:11]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N+:4]([CH2:8][C:9]#[CH:10])([CH2:5][C:6]#[CH:7])[CH2:1][C:2]#[CH:3])=[CH:26][CH:25]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 23351TripropargylamineHCID 230521791-(Bromomethyl)-4-(dodecyloxy)benzene

Product 1

HCID 866815384-(Dodecyloxy)benzyltripropargylammonium bromideYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Tripropargylamine (0.85 mL, 9 mmol) in acetone (6 mL) was slowly added to a solution of 4-(dodecyloxy)benzyl bromide (3.01 g, 8.5 mmol) in acetone (10 mL). After 3 d at room temperature, acetone was removed in vacuo and the residue purified by column chromatography over silica gel with CH2Cl2/MeOH=20/1 to 10/1 as the eluents to give a white powder (2.1 g, 61%). 1H NMR (400 MHz, CDCl3, δ): 7.56 (d, J=8.4 Hz, 2H), 7.08 (d, J=8.4 Hz, 2H), 4.62 (s, 2H), 4.32 (s, 6H), 4.22 (s, 3H), 4.02 (t, J=6.4 Hz, 2H), 1.73-1.68 (m, 2H), 1.40-1.24 (m, 18H), 0.87 (t, J=5.6 Hz, 3H); 13C NMR (100 MHz, CDCl3, δ) 161.6, 134.2, 130.4, 117.2, 115.5, 114.7, 76.6, 75.3, 68.3, 68.0, 63.5, 49.7, 41.9, 29.6, 29.4, 29.3, 29.1, 26, 22.7, 14.1; ESI-MS (m/z): [M−Br]+ calcd for C28H40NO+ 406, found 406.

Workup

  1. customacetone was removed in vacuo
  2. customthe residue purified by column chromatography over silica gel with CH2Cl2/MeOH=20/1 to 10/1 as the eluents

Sources & evidence

ORD record
ord-4250c5dc6d5940649875c35865d5ba8a
Source dataset
uspto-grants-2014_07
Patent number
US08790621B2

Reaction notes

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