Sodium cyanoborohydride → HCID 15524191, compound

HRID 1106427Notes

Reaction equation

HRID 1106427 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6]N[CH2:8]2.[C:17]([BH3-])#[N:18].[Na+]>CO.O>[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][N:18]([CH2:17][CH2:5][C:4]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:3]=1)[CH2:8]2

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 21253084HCID 21253084, compound

Product 1

HCID 15524191HCID 15524191, compoundYield 190.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of the product from Example 5 (1 g, 3.24 mmol) and phenylacetylaldehyde (0.82 ml, 7 mmol) in 2:1 MeOH/H2O (50 mL) was treated with sodium cyanoborohydride (0.56 g, 9 mmol) portionwise under nitrogen and stirred for one hour. The reaction mixture was then cooled under an ice bath and precipitate filtered off. The solids were washed with hexane and oven dried to give the title compound (1.16 g, 95% yield) as an orange solid, mp=120-122° C.

Workup

  1. temperatureThe reaction mixture was then cooled under an ice bath
  2. filtrationprecipitate filtered off
  3. washThe solids were washed with hexane and oven
  4. customdried

Sources & evidence

ORD record
ord-fafda061af9644329d72ed6486bfa0ed
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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