4-chloro-N-methylpiperidine → HCID 57535470, compound

HRID 1455538Notes

Reaction equation

HRID 1455538 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[F:9][C:10]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12](Cl)=[O:13]>C1COCC1.BrC(Br)C>[F:9][C:10]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12]([CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1)=[O:13]

Participants

5

Reactant 2

HCID 793424-chloro-N-methylpiperidineHCID 27782042-Fluoro-5-iodobenzoyl chloride

Product 1

HCID 57535470HCID 57535470, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

A stirred suspension of Mg turnings (3.82 g, 157 mmol) in dry THF, under N2, was treated with 2-3 drops of dibromoethane, followed by slow addition of freshly-distilled 4-chloro-N-methylpiperidine (7.00 g, 52.4 mmol) in THF. The reaction mixture was heated at 70° C. for 3 h, cooled to room temperature, added to 2-fluoro-5-iodobenzoyl chloride (10.1 g, 35.6 mmol) in THF at −78° C., warmed to room temperature over 1 h and concentrated in vacuo. The resultant residue was dissolved in EtOAc, washed with brine, dried over Na2SO4 concentrated in vacuo. This residue was purified by chromatography (0-10% CH2Cl2 in CH3OH as eluent) to provide the title compound (6.50 g, 53%), characterized by HNMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. temperaturewarmed to room temperature over 1 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resultant residue was dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThis residue was purified by chromatography (0-10% CH2Cl2 in CH3OH as eluent)

Sources & evidence

ORD record
ord-1c6a7eadfe304f4f99d9f1f0b387fd3d
Source dataset
uspto-grants-2009_01
Patent number
US07482461B2

Reaction notes

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