Diisopropylethylamine → HCID 66792697, compound

HRID 534905Notes

Reaction equation

HRID 534905 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].C(N(C(C)C)CC)(C)C.Cl.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](Cl)=[O:36]>C(Cl)Cl>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)=[O:36])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66792697HCID 66792697, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(2-tert-butylphenyl)piperazine dihydrochloride (0.064 g, 0.22 mmol) and diisopropylethylamine (0.089 g, 0.69 mmol) in methylene chloride stirring at 0° C. was added picolinoyl chloride hydrochloride (0.043 g, 0.24 mmol) at room temperature. After 2 h the reaction mixture was concentrated under reduced pressure and the residue purified by flash column chromatography (silica gel, 95:5 to 90:10 dichloromethane/methanol) to provide (4-(2-tert-butylphenyl)piperazin-1-yl)(pyridin-2-yl)methanone (0.057 g, 80%) as a brown solid, mp 140-145° C.

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by flash column chromatography (silica gel, 95:5 to 90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-de42e9ffa267482cba9b84e3b4be3914
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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