Triethylamine → hexadecyl N-(2-morpholinoethyl)carbamate

HRID 398743Notes

Reaction equation

HRID 398743 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C(N(CC)CC)C.Cl[C:18]([O: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][CH3:36])=[O:19]>C(Cl)(Cl)Cl>[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:1][C:18](=[O:19])[O: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][CH3:36])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97633Cetyl chloroformateHCID 4082852-Morpholinoethylamine

Product 1

HCID 18968659hexadecyl N-(2-morpholinoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

8.6 Grams of N-(2-aminoethyl)morpholine, 7.2 g of triethylamine and 120 ml of chloroform were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and stirred with ice cooling. To the resulting solution was slowly added dropwise 18.2 g of hexadecyl chloroformate. After completion of the addition, the temperature of the solution was returned to room temperature, followed by refluxing with heating for 0.5 hour. The reaction mixture was cooled to room temperature, washed with water, dried over anhydrous magnesium sulfate and, then, concentrated under reduced pressure. The residue was recrystallized from acetonitrile to obtain 21.1 g of the desired product. m.p. 65° C.

Workup

  1. customequipped with a stirrer, a condenser and a calcium chloride drying tube
  2. additionAfter completion of the addition
  3. customwas returned to room temperature
  4. temperatureby refluxing
  5. temperaturewith heating for 0.5 hour
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8468dbbf0db54cf2839884f6fb65888e
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

Loading…