Isobutylamine → HCID 19043494, compound

HRID 1683329Notes

Reaction equation

HRID 1683329 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[CH3:6][C:7]1([CH3:15])[CH2:13][C:12](=O)[O:11][C:9](=[O:10])[CH2:8]1.C(OC(=O)C)(=O)C.[OH-].[Na+]>C(OCC)C>[CH3:3][CH:2]([CH3:4])[CH2:1][N:5]1[C:9](=[O:10])[CH2:8][C:7]([CH3:15])([CH3:6])[CH2:13][C:12]1=[O:11]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 778133,3-Dimethylglutaric anhydride

Product 1

HCID 19043494HCID 19043494, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Isobutylamine (7.3 g, 0.1 mol) was added slowly to 3,3-dimethylglutaric anhydride (14.2 g, 0.1 mol) stirring at room temperature in a two neck round bottom flask fitted with a water condenser. After 30 minutes, acetic anhydride (20.4 g, 0.2 mol) was added, and the resulting mixture was boiled for two hours. After cooling, the mixture was poured slowly on to an aqueous NaOH solution (2N, 100 ml) stirring at room temperature. After one hour, the mixture was diluted with diethyl ether (50 ml), and the organic layer was separated. The aqueous layer was washed with more diethyl ether (2×50 ml), and the combined organic layer dried and concentrated to give the title compound as a pale yellow oil which solidified on standing, m.p. 48°-52° C., yield 18.5 g (94%). The product was suffuciently pure by NMR spectroscopy to be used directly in the following procedure.

Workup

  1. customfitted with a water condenser
  2. waitthe resulting mixture was boiled for two hours
  3. temperatureAfter cooling
  4. stirringstirring at room temperature
  5. waitAfter one hour
  6. customthe organic layer was separated
  7. washThe aqueous layer was washed with more diethyl ether (2×50 ml)
  8. customthe combined organic layer dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d6cd4f7509204b96a07ba2a093227bf0
Source dataset
uspto-grants-1997_06
Patent number
US05637718

Reaction notes

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