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Water → 8-[(3,4-Dihydro-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

HRID 2072475
Notes
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Reaction equation

HRID 2072475 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][N:12]1[CH2:22][CH2:21][C:15]2([NH:19][CH:18]=[N:17][C:16]2=[O:20])[CH2:14][CH2:13]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][N:12]1[CH2:22][CH2:21][C:15]2([N:19]([C:1]3[CH:10]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:18][NH:17][C:16]2=[O:20])[CH2:14][CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178517902HCID 178517902, compound

Product 1

HCID 214082128-[(3,4-Dihydro-2-naphthalenyl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

A solution of 8-[(3,4-dihydro-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]dec-2-en-4-one (5.0 g) in dry tetrahydrofuran (30 ml) is added dropwise to a slurry of lithium aluminum hydride (0.5 g) in tetrahydrofuran (60 ml). The resulting mixture is refluxed under nitrogen for 16 hours. The reaction mixture is cooled and treated, in order, with water (0.6 ml), 15% sodium hydroxide solution (0.6 ml), and water (1.8 ml). The resulting mixture is stirred for 30 minutes. The mixture is filtered and the solids washed with chloroform. The filtrate is washed with brine, dried over sodium sulfate, and concentrated to give the title compound.

Workup

  1. temperatureThe resulting mixture is refluxed under nitrogen for 16 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe mixture is filtered
  4. washthe solids washed with chloroform
  5. washThe filtrate is washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fac05a3abd8748a39bc815f8aa185f54
Source dataset
uspto-grants-1977_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04051248

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes