Ammonium Acetate → HCID 66649229, compound

HRID 254764Notes

Reaction equation

HRID 254764 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-c7e7385712774cf39d14462a8f0b838e
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

Loading…