Morpholine → Morpholine, 4-(3-methyl-1,3-butadienyl)- (8CI,9CI)

HRID 486839Notes

Reaction equation

HRID 486839 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH3:13][C:14]([CH3:18])=[CH:15][CH:16]=O>C1(C)C=CC=CC=1>[CH3:18][C:14](=[CH2:13])[CH:15]=[CH:16][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 610203-Methyl-2-butenal

Product 1

HCID 586771Morpholine, 4-(3-methyl-1,3-butadienyl)- (8CI,9CI)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous potassium carbonate (43.5 mmol; 6 g) and morpholine (308 mmol; 26.8 g) were introduced into a 100-ml Erlenmeyer equipped with a dropping funnel, under an inert atmosphere. When the reaction medium had been cooled to 0° C., prenal (150 mmol) in toluene (20 ml) was added dropwise. The temperature was allowed to rise to 20° C. and stirring was continued for 4 hours. The potassium carbonate was separated by filtration. The toluene was removed at atmospheric pressure, which permits cracking of the aminal. Under reduced pressure, the excess morpholine was distilled first, and then the expected dienamine (b.p. 108°-110° C. at 20 mm Hg) was distilled.

Workup

  1. customequipped with a dropping funnel, under an inert atmosphere
  2. customto rise to 20° C.
  3. customThe potassium carbonate was separated by filtration
  4. customThe toluene was removed at atmospheric pressure, which
  5. distillationUnder reduced pressure, the excess morpholine was distilled first
  6. distillationthe expected dienamine (b.p. 108°-110° C. at 20 mm Hg) was distilled

Sources & evidence

ORD record
ord-cab6972fc8884bc09b38c60c34d1b733
Source dataset
uspto-grants-1994_03
Patent number
US05292897

Reaction notes

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