Isobutylamine → HCID 74949038, compound

HRID 1513549Notes

Reaction equation

HRID 1513549 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][CH:10]=[CH:11][CH:12]=[CH:13][CH3:14])[CH2:3][C:4]([O:6]C)=O.[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17]>>[CH2:15]([NH:19][C:4](=[O:6])[CH2:3][CH:2]([OH:1])[CH2:8][CH2:9][CH:10]=[CH:11][CH:12]=[CH:13][CH3:14])[CH:16]([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 6558IsobutylamineHCID 76714893HCID 76714893, compound

Product 1

HCID 74949038HCID 74949038, compoundYield 82%

Conditions

Temperature
90 °C

Procedure

Methyl 3-hydroxy-6,8-decadienoate (9) (86.1 g, 0.43 mol) and isobutylamine (95.3 g, 1.3 mol) were put into a 500 ml capacity flask equipped with a stirrer, a thermometer and a reflux condenser, followed by heating to 90° C. and stirring for 24 hours. After recovering isobutylamine under a reduced pressure, and when heptane (700 ml) was added, followed by cooling to 0° C., a white solid was precipitated. This solid was filtered and dried under a reduced pressure to obtain N-isobutyl-3-hydroxy-6,8-decadienamide (10) (85.2 g, 0.35 mol, yield 82%).

Workup

  1. customequipped with a stirrer
  2. customAfter recovering isobutylamine under a reduced pressure, and when heptane (700 ml)
  3. additionwas added
  4. temperatureby cooling to 0° C.
  5. customa white solid was precipitated
  6. filtrationThis solid was filtered
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-9e1e61a6ee72409bb29ed69ca2b61eeb
Source dataset
uspto-grants-2012_07
Patent number
US08217192B2

Reaction notes

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