Piperidine → 1-{[6-(4-Phenylbutoxy)-2-naphthyl]methyl}piperidine

HRID 243817Notes

Reaction equation

HRID 243817 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:9]1([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([CH:30]=O)[CH:24]=[CH:23]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClC(Cl)C>[C:9]1([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([CH2:30][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:24]=[CH:23]3)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 860876276-(4-Phenylbutoxy)-2-formylnaphthalene

Product 1

HCID 666897451-{[6-(4-Phenylbutoxy)-2-naphthyl]methyl}piperidine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution in 6-(4-phenylbutoxy)-2-formylnaphthalene (50 mg) in dichloroethane (0.5 mL), piperidine (20 μL) and triacetoxy sodium borohydride (72 mg) were added, followed by stirring at room temperature for 18 hours. The reaction mixture was added with a 1N aqueous sodium hydroxide solution, and then the mixture was extracted with chloroform. After concentrating the organic layer, the obtained residue was purified by silica gel column chromatography (dichloroform:methanol:acetic acid=120:10:1) to give the title compound (60 mg) having the following physical properties.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. concentrationAfter concentrating the organic layer
  3. customthe obtained residue was purified by silica gel column chromatography (dichloroform:methanol:acetic acid=120:10:1)

Sources & evidence

ORD record
ord-e9bfc041ad43427d9dda5755cd88dfad
Source dataset
uspto-grants-2014_02
Patent number
US08653305B2

Reaction notes

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