Iodine → HCID 58941090, compound

HRID 506864Notes

Reaction equation

HRID 506864 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].[I:15]I.S([O-])([O-])=O.[Na+].[Na+]>C1COCC1.[H-].[Cl-].C1([Zr+2]C2CC=CC=2)CC=CC=1>[I:15]/[CH:2]=[CH:1]/[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 807IodineHCID 24437Sodium SulfiteHCID 122491571-(4-ethynylphenyl)piperidine

Product 1

HCID 58941090HCID 58941090, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 178420572HCID 178420572, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

1-(4-Ethynylphenyl)piperidine (3.49 g, 18.8 mmol) in dry THF (100 mL) was added to a suspension of bis(cyclopentdienyl)zirconium(IV)chloride hydride (5.09 g, 19.76 mmol) in THF (50 mL) at r.t. under nitrogen in the dark. After 1 h, iodine (3.65 g, 23.7 mmol) was added. After a further 2 h, saturated aqueous sodium sulfite (50 mL) was carefully added and the reaction mixture was partitioned between water (30 mL) and EtOAc (100 mL). The organic layer was separated and dried (MgSO4), filtered and concentrated. Purification by column chromatography (5% EtOAc in PE) gave the title compound (3.08 g, 52%) as a colorless-solid. 1H NMR (CDCl3) 1.61 (2H, m), 1.70 (4H, m), 3.20 (4H, m), 6.54 (1H, d), 6.83 (2H, d), 7.19 (2H, d), 7.31 (1H, d).

Workup

  1. waitAfter a further 2 h
  2. customthe reaction mixture was partitioned between water (30 mL) and EtOAc (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (5% EtOAc in PE)

Sources & evidence

ORD record
ord-d95caa8238d24e8b9532c98ff0fbeab7
Source dataset
uspto-grants-2010_08
Patent number
US07786120B2

Reaction notes

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