Ammonia → 2,4-Diethyl-4-methyl-1,5-diazaspiro[5.5]undec-1-ene

HRID 839996Notes

Reaction equation

HRID 839996 reaction equation
[NH2:1][C:2]([CH3:10])([CH2:8][CH3:9])[CH2:3][C:4](=O)[CH2:5][CH3:6].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[Br-].[NH4+:19].N.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:5]([C:4]1[CH2:3][C:2]([CH2:8][CH3:9])([CH3:10])[NH:1][C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[N:19]=1)[CH3:6]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 7967CyclohexanoneHCID 11430Potassium CarbonateHCID 25514Ammonium BromideHCID 213304575-Amino-5-methylheptan-3-one

Product 1

HCID 213304542,4-Diethyl-4-methyl-1,5-diazaspiro[5.5]undec-1-ene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.3 g of the 5-amino-5-methyl-3-heptanone thus obtained were dissolved in 100 ml of methanol, and 10.0 g of cyclohexanone and 10.0 g of ammonium bromide were added to the resulting solution. Dry ammonia was then introduced into the solution at room temperature for 6 hours. The solution was then allowed to stand overnight, after which 10.0 g of potassium carbonate were added and the methanol was removed by evaporation under reduced pressure. The residue was extracted with benzene, and the benzene extract was washed with water and then dried over potassium carbonate. After removing the benzene, the residue was distilled under reduced pressure, giving 14.0 of 2,4-diethyl-4-methyl-1,5-diazaspiro[5.5]undec-1-ene (bp 93° - 94° C/1.5 mmHg).

Workup

  1. customthe methanol was removed by evaporation under reduced pressure
  2. extractionThe residue was extracted with benzene
  3. extractionthe benzene extract
  4. washwas washed with water
  5. dry with materialdried over potassium carbonate
  6. customAfter removing the benzene
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cb6c15dbdd7a4a17b5dcec5fb6bee2e8
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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