2-Ethylhexylamine → HCID 67992145, compound

HRID 1748695Notes

Reaction equation

HRID 1748695 reaction equation
[CH2:1]([O:7][C:8](=[O:21])[C:9]([CH2:11][C:12]([O:14]CCCCCC)=O)=[CH2:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:22]([CH:24]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25][NH2:26])[CH3:23]>>[CH2:1]([O:7][C:8]([CH:9]1[CH2:11][C:12](=[O:14])[N:26]([CH2:25][CH:24]([CH2:22][CH3:23])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:10]1)=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 77192-EthylhexylamineHCID 261107dihexyl 2-methylidenebutanedioate

Product 1

HCID 67992145HCID 67992145, compound

Conditions

Temperature
45 °C

Procedure

Bis(hexyl)itaconate (400 g; 1.34 Mol) was charged to a 1 L reaction vessel and the material stirred mechanically under nitrogen while heating to 45° C. 2-Ethylhexylamine (1.05 equiv.; 1.41 Mol; 182 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. 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 90° C. under reduced pressure (−25″ Hg) (−635 mm) in order to remove hexanol and excess amine. When stripping was complete, H-NMR analysis of the product was consistent with the expected lactam structure. 136.6 g was recovered of yellow moderately viscous liquid. Sample materials were collected from this preparation and designated 1-(2-ethylhexyl)-5-oxo-3-pyrrolidinecarboxylic acid hexyl ester for comparison testing described in the Examples below.

Workup

  1. additionDuring the addition
  2. additionWhen the addition
  3. temperaturethe mixture was heated to 75° C.
  4. temperaturebefore cooling to room temperature overnight
  5. customThe following day, the vessel was equipped with a distillation sidearm/condenser
  6. temperatureheated to 90° C. under reduced pressure (−25″ Hg) (−635 mm) in order
  7. customto remove hexanol and excess amine
  8. custom136.6 g was recovered of yellow moderately viscous liquid
  9. customSample materials were collected from this preparation

Sources & evidence

ORD record
ord-376cd01ff8c441b8a436e3fc5737809a
Source dataset
uspto-grants-2015_10
Patent number
US09150740B2

Reaction notes

Loading…