Dimedone → HCID 178428472, compound

HRID 485605Notes

Reaction equation

HRID 485605 reaction equation
C(O[C:4]1[CH2:9][CH:8]([CH3:10])[CH2:7][CH2:6][N:5]=1)C.[CH3:11][C:12]1([CH3:20])[CH2:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[CH2:13]1>C(OCC)C>[CH3:11][C:12]1([CH3:20])[CH2:13][C:14](=[O:15])[C:16](=[C:4]2[CH2:9][CH:8]([CH3:10])[CH2:7][CH2:6][NH:5]2)[C:17](=[O:18])[CH2:19]1

Participants

4

Reactant 2

HCID 31358DimedoneHCID 13556628HCID 13556628, compound

Product 1

HCID 178428472HCID 178428472, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-ethoxy-4-methyl-3,4,5,6-tetrahydropyridine (9.27 grams, 0.066 mole) and dimedone (9.20 grams, 0.066 mole) is heated at 112°-113° C. for a 3-hour period. The cooled residue is dissolved in ethyl ether and extracted with three portions of 3N HCl. A solution of 6N sodium hydroxide is added to the strongly acidic solution causing the product to separate as a white solid, with precipitation complete at a final pH of 1. The crude product weighs 4.32 grams on drying and melts at 172°-175° C. Recrystallization from a large volume of cyclohexane gives 2.64 grams of pure material, m.p. 174° C.

Workup

  1. temperatureis heated at 112°-113° C. for a 3-hour period
  2. extractionextracted with three portions of 3N HCl
  3. additionA solution of 6N sodium hydroxide is added to the strongly acidic solution
  4. customto separate as a white solid, with precipitation complete at a final pH of 1
  5. customon drying
  6. customRecrystallization from a large volume of cyclohexane

Sources & evidence

ORD record
ord-a977c2ee830b49ee93d65b2dbb642f36
Source dataset
uspto-grants-1985_08
Patent number
US04537616

Reaction notes

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