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Water → 1,2,3,4-Tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol

HRID 66108
Notes
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Reaction equation

HRID 66108 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[CH2:17][CH2:16]1.O.[OH-].[Na+]>CCOCC>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]2[OH:32])[CH2:17][CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 122701533,4-Dihydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1(2H)-naphthalenoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 227555621,2,3,4-Tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenolYield 95.5%

Reagents, catalysts & solvents

1
HCID 3283Diethyl EtherSolvent2×

Procedure

To a slurry of 0.54 g of lithium aluminum hydride in ether is added a solution of 3,4-dihydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1(2H)-naphthalenone (5.0 g, prepared as described in Example 1A) in 150 ml of warm ether. The resulting mixture is refluxed under a nitrogen atmosphere for 3 hours, cooled in ice, and treated (in order) with 0.55 ml of water, 0.55 ml of 15% sodium hydroxide solution and 1.65 ml of water. This mixture is stirred at room temperature for 30 minutes and the inorganic precipitates removed by filtration. The ether solution is dried over anhydrous sodium sulfate, concentrated in vacuo, and triturated with 1:1 hexane-ether to yield 4.8 g of 1,2,3,4-tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol. One crystallization of this material from cyclohexane yields the trans isomer in pure form as determined by NMR and thin layer chromatography analysis.

Workup

  1. temperatureThe resulting mixture is refluxed under a nitrogen atmosphere for 3 hours
  2. temperaturecooled in ice
  3. customthe inorganic precipitates
  4. customremoved by filtration
  5. dry with materialThe ether solution is dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customtriturated with 1:1 hexane-ether

Sources & evidence

ORD record
ord-60d7759d036e44869b0ce08005c19806
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04130646

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes