Sodium cyanoborohydride → HCID 15524191, compound

HRID 1530839Notes

Reaction equation

HRID 1530839 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-4619477b2c754902913931b33673d084
Source dataset
uspto-grants-2001_03
Patent number
US06197771B1

Reaction notes

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