Acetonitrile → HCID 59264606, compound

HRID 573477Notes

Reaction equation

HRID 573477 reaction equation
Br[C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].O.Cl.[NH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[CH3:7][C:2]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)([CH3:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 2723901Piperonylamine

Product 1

HCID 59264606HCID 59264606, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 2-bromo-2-methylpropanoate (80.87 ml, 5 equiv), 4-piperidone hydrochloride monohydrate (19.6 g, 1 equiv), acetonitrile (200 ml) and potassium carbonate (69.1 g, 4 equiv) was heated at reflux under nitrogen with mechanical stirring for 17.5 h then cooled in an ice bath before adding diethyl ether (100 ml). Filtration through celite followed by flash chromatography (silica, 10-50% ethyl acetate in hexane) and evaporation of the product fractions gave the desired product as a yellow oil (14.28 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen
  3. temperaturethen cooled in an ice bath
  4. filtrationFiltration through celite
  5. customfollowed by flash chromatography (silica, 10-50% ethyl acetate in hexane) and evaporation of the product fractions

Sources & evidence

ORD record
ord-474d69b0b65b4fc499a256a8e1ea85b3
Source dataset
uspto-grants-2015_05
Patent number
US09029383B2

Reaction notes

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