1-Bromooctadecane → N,N-Bis(2-Hydroxyethyl)-N'-Octadecyl-1,3-Propanediamine

HRID 127987

Reaction equation

HRID 127987 reaction equation
[CH2:1](Br)[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].[NH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:28][CH2:29][OH:30])[CH2:25][CH2:26][OH:27]>C(O)C1C=CC=CC=1>[OH:30][CH2:29][CH2:28][N:24]([CH2:25][CH2:26][OH:27])[CH2:23][CH2:22][CH2:21][NH:20][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]

Participants

4

Reactant 2

HCID 82181-BromooctadecaneHCID 21088(3-Aminopropyl)diethanolamine

Product 1

HCID 20433008N,N-Bis(2-Hydroxyethyl)-N'-Octadecyl-1,3-Propanediamine

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

A solution of octadecyl bromide (26.65 g., 80 mM.), N-(3-aminopropyl)diethanolamine (105 g., 640 mM.) and benzyl alcohol (120 ml.) is heated at 130° C. for twenty-three hours. The benzyl alcohol is removed in vacuo (0.1 mm. Hg, and 75° C.) and the residue taken up in methylene chloride (250 ml.). The methylene chloride solution is washed with aqueous sodium hydroxide (1 N) then with brine. It is dried (Na2SO4), concentrated, and distilled; b.p. 242°-246° C. at 0.1 mm Hg. The product is a waxy solid.

Workup

  1. customThe benzyl alcohol is removed in vacuo (0.1 mm. Hg, and 75° C.)
  2. washThe methylene chloride solution is washed with aqueous sodium hydroxide (1 N)
  3. dry with materialIt is dried (Na2SO4)
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-081cf7686d4640d89305cd2c85ebec99
Source dataset
uspto-grants-1981_03
Patent number
US04258061

Linked notes

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