Iodine → HCID 68801661, compound

HRID 1725635Notes

Reaction equation

HRID 1725635 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH:7]1([CH2:10][N:11]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13][C:12]2=[O:24])[CH2:9][CH2:8]1.II.[Br:27]Br>ClCCl>[Br:27][CH:13]1[CH2:14][CH:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][CH2:17][N:11]([CH2:10][CH:7]2[CH2:8][CH2:9]2)[C:12]1=[O:24]

Participants

6

Reactant 4

HCID 807IodineHCID 24408BromineHCID 24819Phosphorus pentachloride2×HCID 68802665HCID 68802665, compound

Product 1

HCID 68801661HCID 68801661, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus pentachloride (0.3 g, 1.44 mmol) was added slowly to a solution of 1-(cyclopropylmethyl)-5-phenylazepan-2-one (0.35 g, 1.44 mmol) in dichloromethane (8 mL) at 0° C. After 1 h, iodine (3.6 mg, 0.01 mmol) and bromine (0.07 mL, 1.44 mmol) were added, and the mixture was allowed to warm to ambient temperature. After 1 h, another 0.3 g of phosphorus pentachloride was added. After an additional 18 h, the reaction was quenched with saturated sodium bicarbonate. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were washed with water (3×), saturated brine, dried over sodium sulfate, filtered and concentrated.

Workup

  1. waitAfter 1 h
  2. waitAfter an additional 18 h
  3. customthe reaction was quenched with saturated sodium bicarbonate
  4. extractionThe mixture was extracted with dichloromethane (3×)
  5. washthe combined organic extracts were washed with water (3×), saturated brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-91a8cd1abb9c4020966644b7dd08fd9c
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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