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

HRID 616537
Notes
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Reaction equation

HRID 616537 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-87fe7d87698f4025b9c2de6357c6ed4c
Source dataset
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04075165

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes