Dioctadecylamine → 1-(Dioctadecylamino)methyl-4-cyanobenzene

HRID 127995

Reaction equation

HRID 127995 reaction equation
[CH2:1]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=1>C(Cl)(Cl)Cl>[CH2:20]([N:19]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 66989DioctadecylamineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 204329871-(Dioctadecylamino)methyl-4-cyanobenzeneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dioctadecylamine (26.0 g., 0.05 M), α-bromo-p-tolunitrile (4.9 g., 0.025 M) and chloroform (500 ml.) are stirred at room temperature for 24 hours. The precipitate of dioctadecylamine hydrobromide is filtered off and the filtrate concentrated under reduced pressure. The residue is slurried in methanol, filtered, and evaporated to give 1-(dioctadecylamino)methyl-4-cyanobenzene (15.5 g., 97.5% yield).

Workup

  1. filtrationThe precipitate of dioctadecylamine hydrobromide is filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-5ed02cd3ec794e669594e5566a0b3dfc
Source dataset
uspto-grants-1981_03
Patent number
US04258061

Linked notes

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