Hydrochloric Acid → 1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one

HRID 553883Notes

Reaction equation

HRID 553883 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([CH:14]=[CH2:15])[NH:9]2)=[CH:4][CH:3]=1.C(NC(C)C)(C)C.C(Cl)(Cl)Cl.Cl.[C:28](Cl)(=[O:33])[CH2:29][CH2:30][CH:31]=[CH2:32]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([CH:14]=[CH2:15])[N:9]2[C:28](=[O:33])[CH2:29][CH2:30][CH:31]=[CH2:32])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 7912DiisopropylamineHCID 42284934-Pentenoyl chlorideHCID 69010346(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidine

Product 1

HCID 690774171-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidine (460 mg) and diisopropylamine (0.59 mL) in methylene chloride (10 mL), 4-pentenoyl chloride (0.37 mL) was added, and the reaction solution was stirred at room temperature for 1.5 hours. Chloroform and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 307 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with saturated sodium bicarbonate water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-67273f39071b45beac7755d0b0d93619
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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