Propylamine → HCID 12021068, compound

HRID 381194Notes

Reaction equation

HRID 381194 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C([CH:7]([C:21]([O-:23])=O)[C:8]([C:18]([O-:20])=O)([OH:17])[C:9](CC)(CC)[C:10]([O-:12])=O)C>CO>[CH2:1]([NH:4][C:10](=[O:12])[CH2:9][C:8]([CH2:7][C:21]([NH:4][CH2:1][CH2:2][CH3:3])=[O:23])([C:18]([NH:4][CH2:1][CH2:2][CH3:3])=[O:20])[OH:17])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852Propylamine2×HCID 21193475HCID 21193475, compound2×

Product 1

HCID 12021068HCID 12021068, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N′,N″-tri-n-propylcitramide was prepared by the reaction of n-propylamine with triethylcitrate. To a round-bottomed flask were added triethylcitrate (30.245 g; 1 eq), n-propylamine (19.427 g; 3.16 eq) and methanol (40 mL). The clear light yellow solution stirred for 3 days at room temperature prior to the removal of methanol via rotary evaporation at 50° C. The resulting yellow liquid was dried in vacuo at 70° C. and a tacky white solid was obtained. The crude solid was triturated using diethylether, collected via filtration and dried in vacuo to give a white powder with a slight odor (19.19 g; 55% yield).

Workup

  1. customto the removal of methanol
  2. customvia rotary evaporation at 50° C
  3. customThe resulting yellow liquid was dried in vacuo at 70° C.
  4. customa tacky white solid was obtained
  5. customThe crude solid was triturated
  6. filtrationcollected via filtration
  7. customdried in vacuo
  8. customto give a white powder with a slight odor (19.19 g; 55% yield)

Sources & evidence

ORD record
ord-e0242b1d0f134020877d4c1a9099bde5
Source dataset
uspto-grants-2001_10
Patent number
US06306463B1

Reaction notes

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