Ammonia → tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

HRID 735019Notes

Reaction equation

HRID 735019 reaction equation
CNCCNC.Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[I-:25].[Na+].N>O1CCOCC1.[Cu]I>[C:20]([O:19][C:18](=[O:24])[NH:17][C:14]1([C:11]2[CH:12]=[CH:13][C:8]([I:25])=[CH:9][CH:10]=2)[CH2:16][CH2:15]1)([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 53216208tert-Butyl (1-(4-bromophenyl)cyclopropyl)carbamate

Product 1

HCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

0.43 mL (4 mmol) of N,N′-dimethylethylenediamine is added to a reaction mixture of 0.4 g (2 mmol) of copper (I) iodide, 6.2 g (19.86 mmol) of tert-butyl [1-(4-bromophenyl)-cyclopropyl]carbamate, and 6 g (40 mmol) of sodium iodide in 15 mL of 1,4-dioxane and refluxed for 24 hours under nitrogen. Then the cooled suspension is combined with 30% ammonia solution, poured onto distilled water, and extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered, and the solvent is distilled off. Yield: 6.60 g (93% of theory); C14H18INO2 (M=359.20); calc.: molecular ion peak (M+H)+: 360; found: molecular ion peak (M+H)+: 360; Rf value: 0.8 (silica gel, dichloromethane/ethanol (50:1)).

Workup

  1. temperaturerefluxed for 24 hours under nitrogen
  2. additionpoured
  3. distillationonto distilled water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-f352719f350341d8a4c77dce60898658
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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