Acetic Acid → HCID 13609081, compound

HRID 1589243Notes

Reaction equation

HRID 1589243 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C=O.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[C:22](O)(=O)C>C(O)C>[CH:11]([C:7]1[CH:8]=[C:9]([CH2:22][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH2:6])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 32484Diisopropylaniline

Product 1

HCID 13609081HCID 13609081, compoundYield 128%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the conditions described by Miocque and Vierfond (Bull. Soc. Chim. France 1970, 1896), 2,6-diisopropylaniline (17.73 g, 0.10 mol), 37% aqueous formaldehyde (8.1 mL, 0.10 mol), piperidine (8.52 g, 0.10 mol), acetic acid (3.00 g, 0.05 mol), and ethanol (25 mL) were allowed to boil together until the temperature of the solution reached 92° C. The solution was then refluxed for 24 hours. The product was distilled under vacuum (122°-140° C. at 0.7-0.8 mm) to give the title compound (17.57 g, 64%).

Workup

  1. customreached 92° C
  2. temperatureThe solution was then refluxed for 24 hours
  3. distillationThe product was distilled under vacuum (122°-140° C. at 0.7-0.8 mm)

Sources & evidence

ORD record
ord-e788628901a647f4a5a8acb47d6c97ad
Source dataset
uspto-grants-1986_02
Patent number
US04568744

Reaction notes

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