Acetic Acid → HCID 59848712, compound

HRID 599523Notes

Reaction equation

HRID 599523 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:10][N:11]([CH3:16])[CH:12]=[CH:13][CH:14]=[O:15].C=O.[C:19](O)(=O)C>C(O)C>[CH3:10][N:11]([CH3:16])/[CH:12]=[C:13](\[CH2:19][N:7]1[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]1)/[CH:14]=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 780131-IsopropylpiperazineHCID 791253-(Dimethylamino)-2-propenal

Product 1

HCID 59848712HCID 59848712, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1-Isopropylpiperazine (4.4 ml, 30.6 mmol) was added to a solution of 3-(dimethylamino)acrolein (2.82 g, 25.5 mmol) in ethanol (100 ml), followed by formaldehyde (37% solution in water, 2.3 ml, 30.6 mmol) and acetic acid (100 μl). The mixture was stirred at 50° C. for 3.5 hours, then room temperature for 15 hours. The solution was concentrated in vacuo, re-dissolved in ethanol (25 ml) and then formaldehyde (2.3 ml) and acetic acid (100 μl) were added. The mixture was stirred at 60° C. for 4 hours then concentrated in vacuo to yield the title compound as a pale yellow oil (6.10 g, 90%).

Workup

  1. waitroom temperature for 15 hours
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionre-dissolved in ethanol (25 ml)
  4. additionformaldehyde (2.3 ml) and acetic acid (100 μl) were added
  5. stirringThe mixture was stirred at 60° C. for 4 hours
  6. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-c43a664ea5894f7c8c59dda098f33aed
Source dataset
uspto-grants-2011_03
Patent number
US07897778B2

Reaction notes

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