Ammonium Acetate → HCID 66649229, compound

HRID 469867Notes

Reaction equation

HRID 469867 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](=O)[CH3:14])=[CH:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:22].[Na+]>CO>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:13]([NH2:22])[CH3:14])=[CH:7]2

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 10584386HCID 10584386, compound

Product 1

HCID 66649229HCID 66649229, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above ketone (760 mg, 3.689 mmol) was dissolved in methanol (40 ml). Then, ammonium acetate (2.841 g, 36.896 mmol), sodium cyanoborohydride (232 mg, 3.389 mmol) and molecular sieves (3 Å, 7.6 g) were added. The mixture was stirred at room temperature for two days. The solid was filtered and the filtrate was concentrated. The residue was dissolved in water and concentrated aqueous HCl was added dropwise until the pH≈2. The mixture was then extracted with ethyl acetate to remove the unfinished ketone and other by-products. The water layer was basified to pH≈10 with aqueous sodium hydroxide (1M), and was extracted with dichloromethane and the organic layers were combined, dried over magnesium sulfate and concentrated to afford 290 mg of 1-(5,7-difluoro-naphthalen-2-yl)-ethylamine (38% yield).

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in water
  4. additionconcentrated aqueous HCl was added dropwise until the pH≈2
  5. extractionThe mixture was then extracted with ethyl acetate
  6. customto remove the unfinished ketone and other by-products
  7. extractionwas extracted with dichloromethane
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-44cac6158bda41fb95eec6813b16d480
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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