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

HRID 1665980Notes

Reaction equation

HRID 1665980 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-3174d76e71e04f1ca84730d95e7665e8
Source dataset
uspto-grants-2011_10
Patent number
US08039674B2

Reaction notes

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