Iodine → HCID 69054049, compound

HRID 734839Notes

Reaction equation

HRID 734839 reaction equation
[CH2:1]([C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].[I:17]I>C(Cl)Cl.O.O.O.O.O.O.O.O.O.[N+]([O-])([O-])=O.[Fe+2].[N+]([O-])([O-])=O>[I:17][C:15]1[CH:14]=[CH:13][C:4]([O:5][CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)=[C:3]([CH2:1][CH3:2])[CH:16]=1

Participants

5

Reactant 2

HCID 807IodineHCID 64764382HCID 64764382, compound

Product 1

HCID 69054049HCID 69054049, compound

Reagents, catalysts & solvents 2

HCID 129774236HCID 129774236, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A finely triturated mixture of 0.8 g of silica gel (0.2-0.5 mm) and 0.41 g (1.00 mmol) of iron (II) nitrate nonahydrate was added to a solution of 0.44 g (2.01 mmol) of 1-[2-(2-ethylphenoxy)ethyl]pyrrolidine and 0.28 g (1.10 mmol) of iodine in 5 mL of DCM and the mixture was stirred for 12 hours at RT. The reaction mixture was filtered and the filtrate was evaporated down in vacuo. The residue was purified by column chromatography (silica gel, DCM/MeOH/sat. aqueous ammonia 9:1:0.1). Yield: 0.286 g (41% of theoretical); C14H20INO (M=345.219); calc.: molpeak (M+H)+: 346; found: molpeak (M+H)+: 346; HPLC-MS: 6.74 minutes (method A).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated down in vacuo
  3. customThe residue was purified by column chromatography (silica gel, DCM/MeOH/sat. aqueous ammonia 9:1:0.1)
  4. custom6.74 minutes (method A)

Sources & evidence

ORD record
ord-94a9aa8fff9c499cb89c6f68bf341d9c
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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