2-Ethylhexylamine → HCID 86686308, compound

HRID 1748693Notes

Reaction equation

HRID 1748693 reaction equation
[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][O:5][C:6](=[O:21])[C:7]([CH2:9][C:10]([O:12]CC(CC)CCCC)=O)=[CH2:8])[CH3:2].[CH2:26]([CH:28]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:29][NH2:30])[CH3:27]>>[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][O:5][C:6]([CH:7]1[CH2:9][C:10](=[O:12])[N:30]([CH2:29][CH:28]([CH2:26][CH3:27])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:8]1)=[O:21])[CH3:2]

Participants

3

Reactant 2

HCID 77192-EthylhexylamineHCID 261108Bis(2-ethylhexyl) Itaconate

Product 1

HCID 86686308HCID 86686308, compound

Conditions

Temperature
45 °C

Procedure

Bis(2-ethylhexyl)itaconate (400 g; 1.13 Mol) was charged to a 1 L reaction vessel and the material stirred mechanically under nitrogen while heating to 45° C. 2-Ethylhexylamine (1.02 equiv.: 1.15 Mol; 148.7 g) was charged to a pressure-equalizing addition funnel and the amine added dropwise to the stirred diester over the course of one hour. During the addition, a moderate exotherm was observed and the mixture was allowed to heat to 70° C. When the addition was complete, the mixture was heated to 75° C. and held for one hour before cooling to room temperature overnight. The following day, the vessel was equipped with a distillation sidearm/condenser and heated to 120 to 125° C. under reduced pressure (−30″ Hg) (−762 mm) in order to remove 2-ethylhexanol and excess amine. When stripping was complete, the apparatus was backfilled with nitrogen and cooled to room temperature. The amount of 2-ethylhexanol collected was 141.7 g (1.09 Mol; 96.5% of theoretical recovery). The stripped product was warmed to 50° C. and filtered through a 1″ (2.5 cm) plug of silica gel, giving the final product as a light yellow liquid. H-NMR analysis of the product was consistent with the expected product. Sample materials were collected from this preparation and designated 1-(2-ethylhexyl)-5-oxo-3-pyrrolidinecarboxylic acid 2-ethylhexyl ester for comparison testing described in the Examples below.

Workup

  1. additionDuring the addition
  2. temperatureto heat to 70° C
  3. additionWhen the addition
  4. temperaturethe mixture was heated to 75° C.
  5. temperaturebefore cooling to room temperature overnight
  6. customThe following day, the vessel was equipped with a distillation sidearm/condenser
  7. temperatureheated to 120 to 125° C. under reduced pressure (−30″ Hg) (−762 mm) in order
  8. customto remove 2-ethylhexanol and excess amine
  9. temperaturecooled to room temperature
  10. customThe amount of 2-ethylhexanol collected
  11. temperatureThe stripped product was warmed to 50° C.
  12. filtrationfiltered through a 1″ (2.5 cm) plug of silica gel

Sources & evidence

ORD record
ord-6a3b3d03d16946d4aa5c6d1d2e66ebd8
Source dataset
uspto-grants-2015_10
Patent number
US09150740B2

Reaction notes

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