4-Fluorobenzoyl chloride → HCID 66792715, compound

HRID 534907Notes

Reaction equation

HRID 534907 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.[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>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:33]([C:32]2[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=2)=[O:34])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66792715HCID 66792715, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(2-tert-butylphenyl)piperazine dihydrochloride (0.125 g, 0.43 mmol) and diisopropylethylamine (0.171 g, 1.32 mmol) in methylene chloride (5.0 mL) at 0° C. was added 4-fluorobenzoyl chloride (0.080 g, 0.51 mmol) and the reaction mixture was warmed to room temperature. After 2 h the reaction mixture was concentrated under reduced pressure and the residue purified by flash column chromatography (silica gel, 100:0 to 95:5 dichloromethane/methanol) to provided (4-(2-tert-butylphenyl)piperazin-1-yl)(4-fluorophenyl)methanone (0.044 g, 30%) as a white solid, mp 137-139° C.

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by flash column chromatography (silica gel, 100:0 to 95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-1c1e77e55d7d48c190b5ff679a0bd3cd
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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