Sodium Hydroxide → 1-[(2-Methoxy-3-pyridyl)methyl]-4-(2-phenylphenethyl)piperidine

HRID 1837726Notes

Reaction equation

HRID 1837726 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][O:22][C:23]1[C:28]([CH:29]=O)=[CH:27][CH:26]=[CH:25][N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1>[CH3:21][O:22][C:23]1[C:28]([CH2:29][N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][C:8]3[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:16][CH2:15]2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 125333912-Methoxypyridine-3-carbaldehydeHCID 226783264-(2-Phenylphenethyl)piperidine

Product 1

HCID 226784851-[(2-Methoxy-3-pyridyl)methyl]-4-(2-phenylphenethyl)piperidineYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

181 mg of 4-(2-phenylphenethyl)piperidine synthesized from the corresponding raw material in the same manner as in the above-mentioned process, 150 mg of 2-methoxy-3-pyridinecarboxaldehyde and 226 mg of sodium triacetoxy borohydride were suspended in 5 ml of tetrahydrofuran, and the mixture was stirred for 20 hours at room temperature. The reaction mixture was basified by adding a 1N aqueous sodium hydroxide thereto, and then extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:19), to give 213 mg of the title compound as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by NH
  6. customform silica gel column chromatography (ethyl acetate:hexane=1:19)

Sources & evidence

ORD record
ord-2fe2379c764742979db2345616087270
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

Loading…