Potassium Cyanide → HCID 22141273, compound

HRID 1826368Notes

Reaction equation

HRID 1826368 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2([CH3:23])[CH:13]3[CH:9]2[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]3)[CH:5]=[CH:6][CH:7]=1.[C-:24]#[N:25].[K+]>C1(C)C=CC=CC=1>[CH3:23][C:8]1([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[C:24]#[N:25])[CH:13]2[CH:9]1[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:12]2

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 22141185HCID 22141185, compound

Product 1

HCID 22141273HCID 22141273, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of 6-(3-iodophenyl)-6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hexane (Example 86, 490 mg, 1.18 mmol) in toluene (20 ml) was added tetrakistriphenylphosphine palladium (0) (0.68 g, 0.60 mmol) and a finely crushed mixture of potassium cyanide (320 mg, 5.0 mmol) and neutral activated alumina (640 mg) under nitrogen. The reaction mixture was heated to 80° C. for 3 h, and then at reflux for 30 minutes before cooling to room temperature and concentrating in vacuo. The mixture was absorbed onto silica gel (7 g) and then purified by chromatography on silica gel (100 g) eluting with hexane: ethyl acetate (95:5 and then 50:50) to give a red solid (165 mg, 44%).

Workup

  1. temperatureat reflux for 30 minutes
  2. temperaturebefore cooling to room temperature
  3. concentrationconcentrating in vacuo
  4. customThe mixture was absorbed onto silica gel (7 g)
  5. custompurified by chromatography on silica gel (100 g)
  6. washeluting with hexane: ethyl acetate (95:5

Sources & evidence

ORD record
ord-0c0d031414854bc68b4a8de7305f8776
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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