Acetonitrile → HCID 66656004, compound

HRID 1891324Notes

Reaction equation

HRID 1891324 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].CC#N.Cl[C:16]1[N:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[CH:18][CH:17]=1>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:16]2[CH:17]=[CH:18][C:19]([C:22](=[O:24])[CH3:23])=[CH:20][N:21]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 70770Ethyl 4-piperidinecarboxylateHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 66656004HCID 66656004, compoundYield 89.9%

Procedure

To a stirred solution of piperidine-4-carboxylic acid ethyl ester (12.6 g, 0.080 mol) in CH3CN (250 mol), iPr2Net (33.7 mL, 0.193 mol) and 1-(6-chloro-pyridin-3-yl)-ethanone (10 g, 0.064 mol) were added. The reaction mixture was heated at reflux over night, and then volatiles evaporated under high vacuum. Column chromatography (SiO2, EtOAc/heptane, 1:9 to 1:1) yielded 15.9 g (89%) of 5′-acetyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester as a yellow oil. ES-MS m/e: 277.2 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux over night
  3. customvolatiles evaporated under high vacuum

Sources & evidence

ORD record
ord-e305372092de43da9b8c87be746c20cd
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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