Cyanide → 1,1'-Bipiperidine

HRID 2183485Notes

Reaction equation

HRID 2183485 reaction equation
[C-:1]#[N:2].C[Mg+].[Br-].[CH2:6]1[CH2:10]O[CH2:8][CH2:7]1>CCOCC>[N:2]1([N:2]2[CH2:1][CH2:10][CH2:6][CH2:7][CH2:8]2)[CH2:1][CH2:10][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 5975CyanideHCID 8028TetrahydrofuranHCID 178418689HCID 178418689, compound

Product 1

HCID 682791,1'-BipiperidineYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

The cyanide (4.87 g, 15 mmol) was taken up in THF (75 ml). CH3MgBr (25 ml of a 3.0 M solution in Et2O) was added to the reaction mixture at 0° C. The solution was allowed to warm to 25° C. and was stirred at that temperature for 18 h. The solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc. The aqueous layer was extracted with EtOAc. The combined EtOAc layers were washed with brine and dried (Na2SO4). Filtration and concentration gave a yellow oil. Purification via flash chromatography (95/5 to 90/10 EtOAc/MeOH, SiO2) gave 3.7 g (79%) of the piperidino-piperidine 12 as a yellow gum.

Workup

  1. customThe solution was partitioned between 25 wt % aqueous solution of sodium citrate and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and concentration
  6. customgave a yellow oil
  7. customPurification via flash chromatography (95/5 to 90/10 EtOAc/MeOH, SiO2)

Sources & evidence

ORD record
ord-af52f940602c4c93861bc492b875a256
Source dataset
uspto-grants-2005_05
Patent number
US06900211B2

Reaction notes

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