Ethyl Acetate → HCID 22678378, compound

HRID 1837732Notes

Reaction equation

HRID 1837732 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[C:19](=[O:24])[NH:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.Br[CH2:26][CH2:27][CH2:28][C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]3[C:19]([O:24][CH2:26][CH2:27][CH2:28][C:29]#[N:30])=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 22678496HCID 22678496, compound

Product 1

HCID 22678378HCID 22678378, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

200 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(2-oxo-1,2-dihydro-3-pyridinyl)ethyl]piperidine obtained in Example 47,95 mg of γ-bromobutyronitrile and 169 mg of potassium carbonate were suspended in 5 ml of N,N-dimethylformamide, and the mixture was stirred at 60° C. for 4 hours. Ethyl acetate was added thereto, the resulting salt was filtered off, and the solvent was evaporated. The crude product was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:4), to give 77 mg of the title compound as a colorless oil.

Workup

  1. filtrationthe resulting salt was filtered off
  2. customthe solvent was evaporated
  3. customThe crude product was purified by NH
  4. customform silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-8eb386faa9a84e7ba2148939bbf2cdb9
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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