Dioctadecylamine → ethyl 4-Dioctadecylaminobutyrate

HRID 258732Notes

Reaction equation

HRID 258732 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][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]>C1(C)C=CC=CC=1>[CH2:20]([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])[CH2:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[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 76300Ethyl 4-bromobutyrate

Product 1

HCID 20433003ethyl 4-DioctadecylaminobutyrateYield 58.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of dioctadecylamine (5.2 g., 0.01 mole), ethyl 4-bromobutyrate (1.95 g., 0.01 mole) and toluene (50 ml.) is heated at reflux for sixteen hours, then cooled and concentrated in vacuo to a semi-solid oil. The oil is triturated with ethylacetate, filtered, and the filtrate washed with water, then dried (Na2SO4). Removal of the solvent gives the product as an oil (3.7 g.).

Workup

  1. temperatureat reflux for sixteen hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo to a semi-solid oil
  4. customThe oil is triturated with ethylacetate
  5. filtrationfiltered
  6. washthe filtrate washed with water
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-bb039cc302874f38956c18a87722eb24
Source dataset
uspto-grants-1977_07
Patent number
US04034040

Reaction notes

Loading…