Acetyl chloride → 1-[4-(4-Nitrophenyl)-1-piperidinyl]ethanone

HRID 2189272Notes

Reaction equation

HRID 2189272 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16](Cl)([CH3:18])=[O:17].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16](=[O:17])[CH3:18])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 159258174-(4-Nitrophenyl)piperidine

Product 1

HCID 580159481-[4-(4-Nitrophenyl)-1-piperidinyl]ethanoneYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-Nitro-phenyl)-piperidin (206 mg, 1 mmol) in CH2Cl2 (3 mL) is added AcCl (0.106 mL, 1.5 mmol) at 0° C. Then Et3N (0.253 mL, 1.8 mmol) is added slowly. The mixture is stirred at 0° C. for 10 minutes. Then saturated NaHCO3 aqueous solution is added. The aqueous layer is extracted with CH2Cl2, and the organic extracts are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93) to give 273 mg of the title compound as yellow solid.

Workup

  1. extractionThe aqueous layer is extracted with CH2Cl2
  2. dry with materialthe organic extracts are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=0.7:99.3 to 6:93)

Sources & evidence

ORD record
ord-329d257e9d614ed5885aa7661ba30e77
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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