Dioctadecylamine → ethyl 4-Dioctadecylaminobutyrate

HRID 2412359Notes

Reaction equation

HRID 2412359 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-0698acd6f45747f9962ee2d111ca10a4
Source dataset
uspto-grants-1985_01
Patent number
US04491583

Reaction notes

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