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

HRID 727987Notes

Reaction equation

HRID 727987 reaction equation
C([N:4]([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][CH2:38][CH2:39][CH3:40])[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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])C=C.ClC1C=CC=[C:44]([C:48](OO)=[O:49])[CH:43]=1.C(OCC)(=O)C.CO>C(Cl)Cl>[CH2:48]([O:49][N: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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[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][CH2:38][CH2:39][CH3:40])[CH:44]=[CH2:43]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 19925741N-allyl-N,N-dioctadecylamine

Product 1

HCID 21885151N-Octadecyl-N-[(prop-2-en-1-yl)oxy]octadecan-1-amineYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a cooled solution of 5.0 g (9 mmol) of N-allyl-N,N-dioctadecylamine in 50 ml of methylene chloride at 0° C. under a nitrogen atmosphere is added dropwise with stirring a solution of 1.54 g (9 mmol) of 85% active m-chloroperbenzoic acid in 50 ml of methylene chloride. After the addition is complete (approximately 15 minutes), the resultant solution is allowed to warm to ambient temperature (about 22°-24° C.). The reaction is complete after about 5 hours when TLC analysis (silica gel, 19:1 v/v ethyl acetate:methanol)indicates the starting material has completely reacted. The reaction mixture is transferred to a separatory funnel and washed sequentially with three 50 ml portions of 10% aqueous sodium hydroxide solution and then with 100 ml of distilled water. The organic layer is dried over anhydrous sodium sulfate and heated under reflux at approximately 40° C. for two hours. The resultant solution is concentrated in vacuo and the residue is purified by flash chromatography (silica gel, 94:6 v/v hexane:ethyl acetate eluent) to give 3.3 g (64% yield) of the title compound as a white solid melting at 62°-65° C.

Workup

  1. additionAfter the addition
  2. custom(approximately 15 minutes)
  3. customhas completely reacted
  4. customThe reaction mixture is transferred to a separatory funnel
  5. washwashed sequentially with three 50 ml portions of 10% aqueous sodium hydroxide solution
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  7. temperatureheated
  8. temperatureunder reflux at approximately 40° C. for two hours
  9. concentrationThe resultant solution is concentrated in vacuo
  10. customthe residue is purified by flash chromatography (silica gel, 94:6 v/v hexane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-a48caced517043dd8ea6d2244a986ab2
Source dataset
uspto-grants-1991_09
Patent number
US05045583

Reaction notes

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