Isoamylamine → HCID 13007241, compound

HRID 381197Notes

Reaction equation

HRID 381197 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].C([CH:9]([C:23]([O-:25])=O)[C:10]([C:20]([O-:22])=O)([OH:19])[C:11](CC)(CC)[C:12]([O-:14])=O)C>CO>[CH2:1]([NH:6][C:12](=[O:14])[CH2:11][C:10]([CH2:9][C:23]([NH:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])=[O:25])([C:20]([NH:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])=[O:22])[OH:19])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 7894Isoamylamine2×HCID 21193475HCID 21193475, compound2×

Product 1

HCID 13007241HCID 13007241, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N′,N″-tri-iso-amylcitramide was prepared by the reaction of iso-amylamine with triethylcitrate. To a round-bottomed flask were added triethylcitrate (30.001 g, 1 eq), iso-amylamine (28.399 g, 3.0 eq) and methanol (40 mL). The clear light yellow solution stirred for 2 days at room temperature and then additional amine (1.1 eq) was added. After stirring 1 week, a clear yellow solution was observed. Methanol was removed in vacuo and the resulting white solid was triturated using diethylether, collected via filtration and dried in vacuo to give a white powder with a very slight odor (22.52 g, 52.1% yield).

Workup

  1. stirringAfter stirring 1 week
  2. customMethanol was removed in vacuo
  3. customthe resulting white solid was triturated
  4. filtrationcollected via filtration
  5. customdried in vacuo
  6. customto give a white powder with a very slight odor (22.52 g, 52.1% yield)

Sources & evidence

ORD record
ord-f0f1d225a34b42d3bb617d685df62bd5
Source dataset
uspto-grants-2001_10
Patent number
US06306463B1

Reaction notes

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