Potassium Iodide → HCID 9953250, compound

HRID 2119447Notes

Reaction equation

HRID 2119447 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[CH:4][CH:3]=1.[I-].[K+].[BH4-].[Na+]>P(Cl)(Cl)(Cl)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[CH2:19][CH2:18][N:11]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 4311764Sodium borohydrideHCID 234407982-(4-Bromophenyl)-N-{2-(3-methoxyphenyl)ethyl}-N-phenylacetamide

Product 1

HCID 9953250HCID 9953250, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 2-(4-bromophenyl)-N-{2-(3-methoxyphenyl)ethyl}-N-phenylacetamide (1.0 g, 2.4 mmol) in phosphorous oxychloride (10 mL) under nitrogen was heated to 80° C. After 15 hours, the reaction was cooled to RT and slowly poured over ice. Potassium iodide (0.78 g, 4.7 mmol) was then added to the mixture, and after 30 minutes, the quinolinium salt was extracted with ethyl acetate (2×100 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was then dissolved in methanol (25 mL), and sodium borohydride (0.27 g, 7.2 mmol) was slowly added. After 30 minutes, the reaction was concentrated and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered and concentrated to provide the title compound (0.20 g, 21% yield): 1H NMR (CDCl3) 6.6-7.4 (m, 12H), 4.82 (t, 1H), 3.60 (s, 3H), 3.58 (m, 2H), 2.6-3.2 (m 4H); EI−MS (m/z) 407.

Workup

  1. additionslowly poured over ice
  2. waitafter 30 minutes
  3. extractionthe quinolinium salt was extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was then dissolved in methanol (25 mL)
  8. waitAfter 30 minutes
  9. concentrationthe reaction was concentrated
  10. custompartitioned between ethyl acetate and water
  11. dry with materialThe organic layer was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-7c5cdd4af31d438da1ad38ef4b73b28e
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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