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

HRID 978576Notes

Reaction equation

HRID 978576 reaction equation
[CH2:1]([N:8]1[C:19](=O)[CH2:18][C:10]2([C:14](=O)[N:13]([CH3:16])[C:12](=O)[CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:29]>O1CCCC1.C(O)(C)C.O>[ClH:29].[ClH:29].[CH2:1]([N:8]1[CH2:19][CH2:18][C:10]2([CH2:11][CH2:12][N:13]([CH3:16])[CH2:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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-benzyl-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-111b20befedc4398b0ed1d0ba9b36288
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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