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

HRID 890089Notes

Reaction equation

HRID 890089 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-1a4542b600d648cc9fd77c99e36d9cdd
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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