Ammonia → HCID 54274160, compound

HRID 1416523Notes

Reaction equation

HRID 1416523 reaction equation
[CH:1]([C:3]12[CH2:9][N:6]3[CH2:7][CH:8]1[CH:4]2[CH2:5]3)=O.[C-:10]#[N:11].[K+].[NH3:13].[Cl-].[NH4+]>O>[NH2:13][CH:1]([C:3]12[CH2:9][N:6]3[CH2:7][CH:8]1[CH:4]2[CH2:5]3)[C:10]#[N:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 450871594-Azatricyclo[2.2.1.0~2,6~]heptane-1-carbaldehyde

Product 1

HCID 54274160HCID 54274160, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an icecooled solution of 1-formyl-4-azatricyclo[2.2.1.02,6 ]heptane (3.56 g, 29 mmol) in water (5 ml) was added a solution of potassium cyanide (2.08 g, 31.9 mmol) in water (5 ml) over 30 min. After an additional 1 h, cooling was removed and the reaction stirred at room temperature for 16 h. The cyanohydrin product was then added 25% aqueous ammonia (4.0 ml, 52 mmol) and ammonium chloride (7.76 g, 145 mmol). The reaction mixture was stirred at room temperature for 18 h and then extracted with isopropanole/dichloromethane (1:10) (10×75 ml). The organic phases were dried and evaporated to give the title compound as an oil (2.5 g, 58%).

Workup

  1. temperaturecooling
  2. customwas removed
  3. stirringThe reaction mixture was stirred at room temperature for 18 h
  4. extractionextracted with isopropanole/dichloromethane (1:10) (10×75 ml)
  5. customThe organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-cc9378448944404c835f9c103736cf34
Source dataset
uspto-grants-1999_06
Patent number
US05914338

Reaction notes

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