Potassium Cyanide → HCID 67050155, compound

HRID 44460Notes

Reaction equation

HRID 44460 reaction equation
Br.Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]23[CH2:16][N:13]([CH2:14][CH2:15]2)[CH2:12][CH2:11][CH2:10]3)=[CH:5][N:4]=1.[C-:17]#[N:18].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:13]12[CH2:16][C:9]([C:6]3[C:5]([C:17]#[N:18])=[N:4][CH:3]=[CH:8][CH:7]=3)([CH2:15][CH2:14]1)[CH2:10][CH2:11][CH2:12]2

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 86620864HCID 86620864, compound

Product 1

HCID 67050155HCID 67050155, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.5 g (4.3 mmol) of (−)-5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]octane hydrobromide (prepared according to the method described in step 1.2 of Example 1), dissolved in 12 ml of dimethylformamide, 0.42 g (6.46 mmol) of potassium cyanide and 5 g (4.3 mmol) of tetrakis(triphenylphosphine)palladium are successively introduced into a 25 ml reactor. The mixture is then heated at 90° C. for 3 hours and then neutralized with saturated aqueous sodium carbonate solution. The aqueous phase is extracted with chloroform and the combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions. 0.705 g of expected product is thus obtained in the form of an amorphous solid.

Workup

  1. extractionThe aqueous phase is extracted with chloroform
  2. dry with materialthe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a column of silica gel
  6. washeluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions

Sources & evidence

ORD record
ord-18dfa05ca8e04c33b086e49d75a44f3d
Source dataset
uspto-grants-2013_09
Patent number
US08541440B2

Reaction notes

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