Hydrochloric Acid → HCID 18316935, compound

HRID 430818Notes

Reaction equation

HRID 430818 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][C:7](=[O:12])[CH2:8]2.Cl.[Cl-].[NH4+:17].[C-:18]#N.[K+]>O>[C:18]([C:7]1([OH:12])[CH2:6][CH:5]2[N:4]([CH2:3][C:2]([F:1])([F:13])[F:14])[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)#[N:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 25517Ammonium Chloride2×HCID 18519913HCID 18519913, compound

Product 1

HCID 18316935HCID 18316935, compoundYield 113.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A 50 ml 2-necked round bottom flask was fitted with a pressure equalised dropping funnel, bubbler and magnetic stirrer. 8-(2,2,2-Trifluoroethyl)-8-azabicyclo[3.2.1]octan-3-one (5.23 g, 25 mmol) was charged to the reaction flask and suspended in water (5 ml). Hydrochloric acid (5 ml, 5M) was added followed by solid ammonium chloride (2.15 g) and the mixture stirred until the ammonium chloride had dissolved. The mixture was cooled to 0° C., a solution of potassium cyanide (5.031 g, 75 mmol) in water (7.5 ml) was added over 1 hour and the resulting mixture was then stirred at 0° C. for 2 hours during which time a solid precipitate formed. The precipitate was isolated by filtration and sucked dry for 10 minutes, to give 3-cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane as an off-white solid (6.62 g).

Workup

  1. customA 50 ml 2-necked round bottom flask was fitted with a pressure
  2. dissolutionhad dissolved
  3. customformed
  4. customThe precipitate was isolated by filtration
  5. customsucked dry for 10 minutes

Sources & evidence

ORD record
ord-5ebc33685ec049afb793dc49d42a0af0
Source dataset
uspto-grants-2001_11
Patent number
US06323343B1

Reaction notes

Loading…