Hydrochloric Acid → 2-Benzyl-7-methyl-2,7-diazaspiro[4.4]nonane Dihydrochloride

HRID 2372063Notes

Reaction equation

HRID 2372063 reaction equation
[C:1]1([CH2:7][N:8]2[C:19](=O)[CH2:18][C:10]3([C:14](=O)[N:13]([CH3:16])[C:12](=O)[CH2:11]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:29]>O1CCCC1.C(O)(C)C.O>[ClH:29].[ClH:29].[C:1]1([CH2:7][N:8]2[CH2:19][CH2:18][C:10]3([CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28689347-Benzyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 28688372-Benzyl-7-methyl-2,7-diazaspiro[4.4]nonane Dihydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.36 g (5.0 mmol) 7-phenylmethyl-2-methyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione in 50 ml tetrahydrofuran was added dropwise to a suspension of 0.95 g (25 mmol) lithium aluminum hydride in 30 ml tetrahydrofuran. The mixture was stirred overnight at room temperature, refluxed one hour, cooled, and treated dropwise with 0.95 ml water, 0.95 ml 15% sodium hydroxide solution, and 2.8 ml water. After removal of the inorganic solids by filtration, the filtrate was concentrated in vacuo to give a syrup which was dissolved in isopropanol and treated with excess 6N hydrogen chloride in isopropanol. Crystallization afforded 0.97 g of the title compound, mp 233-234° C.

Workup

  1. temperaturerefluxed one hour
  2. temperaturecooled
  3. customAfter removal of the inorganic solids
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a syrup which
  7. customCrystallization

Sources & evidence

ORD record
ord-6fb2c0e236df4727b42b477d3bba437f
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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