Ammonium Acetate → HCID 63198208, compound

HRID 623312Notes

Reaction equation

HRID 623312 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][C:13](=O)CC)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:17]([O-])(=O)C.[NH4+].[C:22]([BH3-])#[N:23].[Na+]>CO>[Cl:1][C:2]1[C:3]([CH:12]([CH3:13])[CH:22]([NH2:23])[CH3:17])=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 63199034HCID 63199034, compound

Product 1

HCID 63198208HCID 63198208, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.64 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) (0.0025 mol) were diluted in 5 mL of methanol. 7.0 g of molecular sieves 3 Å, 1.90 g (0.025 mol) of ammonium acetate and 0.39 g (0.0052 mol) of sodium cyanoborohydride were added. The reaction medium was stirred overnight at room temperature. After filtration, the pH was adjusted to 9 with an aqueous solution of 1 N sodium hydroxide. The reaction mixture was concentrated to dryness and 30 mL of ethyl acetate were added. The organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water; dried over magnesium sulfate, filtered and concentrated to dryness. The crude material was dissolved in 15 mL of 1 N hydrochloric acid and extracted with 15 mL of ethyl acetate. An aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which was subsequently extracted twice with 15 mL of ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness. 0.21 g (32%) of desired product 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine (IIa-16) were obtained, [M+1]=253.

Workup

  1. filtrationAfter filtration
  2. concentrationThe reaction mixture was concentrated to dryness and 30 mL of ethyl acetate
  3. additionwere added
  4. washThe organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. dissolutionThe crude material was dissolved in 15 mL of 1 N hydrochloric acid
  9. extractionextracted with 15 mL of ethyl acetate
  10. additionAn aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which
  11. extractionwas subsequently extracted twice with 15 mL of ethyl acetate
  12. dry with materialThe organic phase was dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c28bac0a8e704250bf682045155cbcca
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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