Acrylonitrile → 1,3-Di(n-hexadecyloxy)-2-(2-cyanoethylamino)propane

HRID 261594Notes

Reaction equation

HRID 261594 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([NH2:38])[CH2:20][O: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][CH3:16].[C:39](#[N:42])[CH:40]=[CH2:41].[OH-].[Na+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:1]([O:17][CH2:18][CH:19]([NH:38][CH2:41][CH2:40][C:39]#[N:42])[CH2:20][O: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][CH3:16]

Participants

5

Reactant 4

HCID 7855Acrylonitrile2×HCID 14798Sodium Hydroxide2×HCID 2723671Tetrabutylammonium HydroxideHCID 184272321,3-Dihexadecyloxy-2-aminopropane

Product 1

HCID 234661191,3-Di(n-hexadecyloxy)-2-(2-cyanoethylamino)propaneYield 36%

Conditions

Temperature
60 °C

Procedure

A mixture of 1,3-di(n-hexadecyloxy)-2-aminopropane (500 mg., 0.93 mmoles), acrylonitrile (75 ml.) and 2 wt. % aqueous sodium hydroxide solution (75 ml.) was heated to 60° C. Tetrabutyl ammonium hydroxide (1 ml. of 40 wt. % aqueous solution) was then added and the resulting mixture stirred for 15 minutes at 90° C. The reaction mixture was then cooled, causing precipitation of solids, which were isolated by filtration and found (TLC) to contain a large quantity of unreacted starting material. Using fresh acrylonitrile and aqueous sodium hydroxide solution in each cycle, the solids were treated two more times by the above procedure. The third cycle solid product was purified by silica gel chromatography (elution with toluene:ethyl acetate) [200 mg., 36% yield, m.p. 45°-46° C., ir (CHCl3) 2250 cm-1, n.m.r. (CDCl3) δ 3.07 (t, 2, --NHCH2CH2CN) and 2.53 (t, 2, --NHCH2CH2CN)].

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customprecipitation of solids
  3. customwhich were isolated by filtration
  4. additionthe solids were treated two more times by the above procedure
  5. customThe third cycle solid product was purified by silica gel chromatography (elution with toluene:ethyl acetate) [200 mg., 36% yield, m.p. 45°-46° C., ir (CHCl3) 2250 cm-1, n.m.r. (CDCl3) δ 3.07 (t, 2, --NHCH2CH2CN) and 2.53 (t, 2, --NHCH2CH2CN)]

Sources & evidence

ORD record
ord-48cf32f3f3ff486aa4ecf992da01935b
Source dataset
uspto-grants-1979_08
Patent number
US04166132

Reaction notes

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