Pyridine → HCID 66792838, compound

HRID 534911Notes

Reaction equation

HRID 534911 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].N1C=CC=CC=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[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:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:32])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66792838HCID 66792838, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(2-tert-butylphenyl)piperazine dihydrochloride (0.150 g, 0.52 mmol) and pyridine (0.166 g, 2.13 mmol) in dichloromethane (5 mL) was added benzoyl chloride (0.079 g, 0.56 mmol) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 90:10 to 70:30 heptanes/ethyl acetate, gradient elution) to provide [4-(2-tert-butylphenyl)piperazin-1-yl](phenyl)methanone (0.140 g, 83%) as a white powder, mp 104-106° C.

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography (silica gel, 90:10 to 70:30 heptanes/ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-04fcfb65a53243acb0c58f916117e567
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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