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

HRID 1391230Notes

Reaction equation

HRID 1391230 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-eneYield 63.1%

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 a period of 6 hours. After allowing the solution to stand overnight, 10.0 g of potassium carbonate were added and the methanol was then removed by distillation under reduced pressure. The residue was extracted with benzene, washed with water and dried over potassium carbonate. The benzene was then removed and the residue was distilled under reduced pressure, giving 14.0 g 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 then removed by distillation under reduced pressure
  2. extractionThe residue was extracted with benzene
  3. washwashed with water
  4. dry with materialdried over potassium carbonate
  5. customThe benzene was then removed
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-af14bfe7c34a4b3995ce25688504f336
Source dataset
uspto-grants-1979_02
Patent number
US04141883

Reaction notes

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