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

HRID 464975Notes

Reaction equation

HRID 464975 reaction equation
[CH3:1][N:2]1[C:6](=O)[CH2:5][C:4]2([CH2:11][C:10](=O)[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:8]2)[C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[ClH:29]>O1CCCC1.C(O)(C)C.O>[ClH:29].[ClH:29].[CH3:1][N:2]1[CH2:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:8]2)[CH2:3]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) 2-methyl-7-(phenylmethyl)-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 2-methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]nonane dihydrochloride, 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-9aefb01537034b9896081e6f967cef1b
Source dataset
uspto-grants-1985_10
Patent number
US04550103

Reaction notes

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