Allyl bromide → N-Octadecyl-N-[(prop-2-en-1-yl)oxy]octadecan-1-amine

HRID 727986Notes

Reaction equation

HRID 727986 reaction equation
[CH2:1]([N:19]([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][CH2:37][CH3:38])[OH:20])[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].[CH2:39](Br)[CH:40]=[CH2:41].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(Cl)(Cl)Cl>[CH2:41]([O:20][N:19]([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][CH2:37][CH3:38])[CH:40]=[CH2:39]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 3507778Bis(octadecyl)hydroxylamine2×

Product 1

HCID 21885151N-Octadecyl-N-[(prop-2-en-1-yl)oxy]octadecan-1-amineYield 36%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 42.4 g (80 mmol) of N,N-dioctadecylhydroxylamine, 13 ml (150 mmol) of allyl bromide and 17.0 g (160 mmol) of sodium carbonate in 450 ml of ethanol is heated under reflux at approximately 80° to 85° C. The reaction is considered complete after 14 hours upon complete disappearance of the N,N-dioctadecylhydroxylamine as indicated by TLC analysis (silica gel, chloroform solvent). The reaction mixture is concentrated under reduced pressure and the resultant residue is triturated with 500 ml of chloroform. The insoluble salts are removed by filtration and the filtrate concentrated. The resultant residue is purified by flash chromatography (silica gel, chloroform solvent) to give 16.6 g (36% yield) of the title compound as a white solid melting at 60°-62° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux at approximately 80° to 85° C
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe resultant residue is triturated with 500 ml of chloroform
  5. customThe insoluble salts are removed by filtration
  6. concentrationthe filtrate concentrated
  7. customThe resultant residue is purified by flash chromatography (silica gel, chloroform solvent)

Sources & evidence

ORD record
ord-a966b0288b924ca387cdec9925132118
Source dataset
uspto-grants-1991_09
Patent number
US05045583

Reaction notes

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