Sodium Iodide → HCID 22049115, compound

HRID 1832248Notes

Reaction equation

HRID 1832248 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15].[CH3:17][CH:18]([CH3:34])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:23]=1)=[O:20].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.CCOC(C)=O>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8](=[O:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:31]1[CH2:32][CH2:33][CH:28]([C:24]2[CH:23]=[C:22]([NH:21][C:19](=[O:20])[CH:18]([CH3:17])[CH3:34])[CH:27]=[CH:26][CH:25]=2)[CH2:29][CH2:30]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 167572552-methyl-N-[3-(4-piperidyl)phenyl]propanamideHCID 220485847-Chloro-1-(2-fluorophenyl)heptan-1-one

Product 1

HCID 22049115HCID 22049115, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A 50-mL round-bottom flask was charged with a solution of 7-chloro-1-oxo-1(2-fluorophenyl)heptane (2.42 g, 10.0 mmol), 2-methyl-N-[3-(4-piperidyl)phenyl]propanamide (2.46 g, 10.0 mmol), K2CO3 (2.76 g, 20.0 mmol) and NaI (2.25 g, 15.0 mmol) in DMF (25.0 mL). The mixture was stirred for 10 min at 25° C. and then heated at 100° C. for 12 h, cooled to 25° C. and diluted with EtOAc (100 mL). The reaction mixture was washed with water (4×50 mL) and the aqueous layer was extracted with EtOAc (100 mL). The organic layers were washed with brine (50 mL), dried over MgSO4, concentrated in vacuo and the crude product was purified by chromatography (EtOAc:MeOH 97:3) to give the desired product (3.70 g, 82.0%).

Workup

  1. temperatureheated at 100° C. for 12 h
  2. temperaturecooled to 25° C.
  3. washThe reaction mixture was washed with water (4×50 mL)
  4. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  5. washThe organic layers were washed with brine (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customthe crude product was purified by chromatography (EtOAc:MeOH 97:3)

Sources & evidence

ORD record
ord-1972290d2e4d419cb5ad6a64d80044b4
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

Loading…