Sodium Bicarbonate → 1-(2-Oxo-1,2-dihydro-3-pyridylmethyl)-4-(2-methylphenoxymethyl)piperidine-4-carbonitrile

HRID 914879Notes

Reaction equation

HRID 914879 reaction equation
Cl.[C:2]([C:4]1([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].[O:19]=[C:20]1[C:25]([CH:26]=O)=[CH:24][CH:23]=[CH:22][NH:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.ClCCl>[O:19]=[C:20]1[C:25]([CH2:26][N:7]2[CH2:8][CH2:9][C:4]([CH2:10][O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])([C:2]#[N:3])[CH2:5][CH2:6]2)=[CH:24][CH:23]=[CH:22][NH:21]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehydeHCID 222482184-Cyano-4-(2-methylphenoxymethyl)piperidine hydrochloride

Product 1

HCID 222484881-(2-Oxo-1,2-dihydro-3-pyridylmethyl)-4-(2-methylphenoxymethyl)piperidine-4-carbonitrileYield 5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After then adding 117 mg of the 4-cyano-4-(2-methylphenoxymethyl)piperidine hydrochloride and 70 mg of 2-oxo-1,2-dihydropyridine-3-carboxaldehyde [CAS No. 36404-89-4] to 10 ml of dichloromethane, the mixture was stirred for 20 minutes at room temperature. 139 mg of sodium triacetoxyborohydride was added and the mixture was stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate and chloroform. After drying the organic layer over magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (solvent: chloroform/methanol) to obtain the title compound (7 mg, 5% yield).

Workup

  1. dry with materialAfter drying the organic layer over magnesium sulfate
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe obtained residue was purified by NH silica gel column chromatography (solvent: chloroform/methanol)

Sources & evidence

ORD record
ord-b357bf7e8a534189baf248edcd5f912e
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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