Acetaldehyde → HCID 24947334, compound

HRID 2043335Notes

Reaction equation

HRID 2043335 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([NH:8][CH2:9][C:10]2[NH:11][CH:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH:16](=O)[CH3:17].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[C:3]([F:15])=[C:4]([N:8]([CH2:16][CH3:17])[CH2:9][C:10]2[NH:11][CH:12]=[N:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 62761381HCID 62761381, compound

Product 1

HCID 24947334HCID 24947334, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

(3-Chloro-2-fluoro-phenyl)-(3H-imidazol-4-ylmethyl)-amine (0.24 g, 1 mmol) was dissolved in methanol (15 ml). Then acetaldehyde (0.28 ml, 5 mmol), zinc chloride (0.55 g, 4 mmol) and sodium cyanoborohydride (0.19 g, 3 mmol) were added and the reaction mixture was allowed to stir at 40° C. overnight. After cooling, the reaction mixture was poured onto ammoniumchloride/ice and extracted with ethyl acetate (2 times 50 ml). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: heptane/ethyl acetate=90:10) to yield a light yellow oil (0.16 g, 63%); MS (ISP): 254.1 ((M+H)+.).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto ammoniumchloride/ice
  3. extractionextracted with ethyl acetate (2 times 50 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-de096799a7d5453e94953a6fc4d91b50
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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