Butylamine → HCID 12021069, compound

HRID 381195Notes

Reaction equation

HRID 381195 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C([CH:8]([C:22]([O-:24])=O)[C:9]([C:19]([O-:21])=O)([OH:18])[C:10](CC)(CC)[C:11]([O-:13])=O)C>CO>[CH2:1]([NH:5][C:11](=[O:13])[CH2:10][C:9]([CH2:8][C:22]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:24])([C:19]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:21])[OH:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007Butylamine2×HCID 21193475HCID 21193475, compound2×

Product 1

HCID 12021069HCID 12021069, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N′,N″-tri-n-butylcitramide was prepared by the reaction of n-butylamine with triethylcitrate. To a round-bottomed flask were added triethylcitrate (31.485 g; 0.1140 mole, 1 eq) and methanol (40 mL). To this solution, n-butylamine (24.999 g; 3.00 eq) was slowly poured. The clear light yellow solution stirred for 3 days at room temperature prior to the removal of methanol via rotary evaporation at 60° C. The resulting crude tacky solid was triturated using diethylether, collected via filtration and dried in vacuo to give a white powder with a slight amine odor (23.95 g; 58% yield).

Workup

  1. customto the removal of methanol
  2. customvia rotary evaporation at 60° C
  3. customThe resulting crude tacky solid was triturated
  4. filtrationcollected via filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ff63785f09dd43489d93197a679b3b9d
Source dataset
uspto-grants-2001_10
Patent number
US06306463B1

Reaction notes

Loading…