2-Ethylhexylamine → HCID 67992999, compound
Reaction equation
[C:1]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[C:2]([CH2:4][C:5]([O:7]CCCC)=O)=[CH2:3].[CH2:18]([CH:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][NH2:22])[CH3:19]>>[CH2:14]([O:13][C:1]([CH:2]1[CH2:4][C:5](=[O:7])[N:22]([CH2:21][CH:20]([CH2:18][CH3:19])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3]1)=[O:12])[CH2:15][CH2:16][CH3:17]Participants
Conditions
- Temperature
- 75 °C
Procedure
Bis(butyl) itaconate (400 g; 1.65 Mol) was charged to a 1 L reaction vessel and the material stirred mechanically under nitrogen while heating to 75° C. 2-Ethylhexylamine (1.7 Mol; 219.7 g) was charged to a pressure-equalizing addition funnel and the amine added drop wise to the stirred diester over the course of one hour and stirred at 75° C. for 2 hours after amine addition. The reactor was equipped for distillation and the temperature was increased slowly to 130° C., holding at full vacuum until stripping was complete. Receivers were changed and the pot heated under full vacuum to increase pot temperature to 165 to 185° C. (head temperature 140 to 175° C.). 469.3 g of product 1.58 Mol; 95.6% yield was collected. Sample materials were collected from this preparation and designated 1-(2-ethylhexyl)-5-oxo-3-pyrrolidinecarboxylic acid butyl ester for comparison testing described in the Examples below.
Workup
- customThe reactor was equipped for distillation
- temperaturethe temperature was increased slowly to 130° C.
- temperaturethe pot heated under full vacuum
- temperatureto increase pot temperature to 165 to 185° C. (head temperature 140 to 175° C.)
- custom95.6% yield was collected
- customSample materials were collected from this preparation
Sources & evidence
- ORD record
- ord-205551b3ef1945b284d099101457d72f
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150740B2
Reaction notes
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