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Iodine → 1-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-oxopiperidine

HRID 2072476
Notes
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Reaction equation

HRID 2072476 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.Cl[CH2:9][C:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].II>C(Cl)Cl>[CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:18][CH2:19][C:10]=1[CH2:9][N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 807IodineHCID 10340Sodium CarbonateHCID 337214-PiperidoneHCID 127714333-(Chloromethyl)-1,2-dihydronaphthalene

Product 1

HCID 214082251-[(3,4-Dihydro-2-naphthalenyl)methyl]-4-oxopiperidine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A mixture of 4-piperidone (2.2 g), 3,4-dihydro-2-chloromethylnaphthalene (4.0 g), and powdered sodium carbonate (3.5 g) in tolune (200 ml) containing several crystals of iodine is refluxed for 14 hours with vigorous stirring under nitrogen. The reaction mixture is then cooled, diluted with methylene chloride (100 ml), and filtered. The filtrate is concentrated and the crude product triturated with 1:1 hexane/ether (100 ml) to give the title compound.

Workup

  1. temperatureis refluxed for 14 hours
  2. temperatureThe reaction mixture is then cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe crude product triturated with 1:1 hexane/ether (100 ml)

Sources & evidence

ORD record
ord-368f8c5c12274854af6fdcce13cb5c20
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