Cyanogen Bromide → HCID 86650494, compound

HRID 536661Notes

Reaction equation

HRID 536661 reaction equation
[CH3:1][N:2]1[CH:9]([CH3:10])[CH2:8][C:7]2([CH3:12])[CH2:11][CH:3]1[CH2:4][C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=12.BrC#[N:19]>C(Cl)Cl>[CH3:10][CH:9]1[N:2]([C:1]#[N:19])[CH:3]2[CH2:11][C:7]([CH3:12])([C:6]3[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=3[CH2:4]2)[CH2:8]1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 13409302HCID 13409302, compound

Product 1

HCID 86650494HCID 86650494, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

3,4,6-Trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine (from Example LVI, 1.7 g) dissolved in CH2Cl2 (40 mL) is added to a solution of BrCN (1.17 g) in CH2Cl2 (10 mL) chilled in an ice bath. The cooling bath is removed and the mixture is stirred at ambient temperature for 1 h and at 45° C. for 2 h. After cooling to ambient temperature, the solution is washed with water, 2 M hydrochloric acid, and 10% aqueous K2CO3 solution. The solution is dried (MgSO4), the solvent is removed, and the residue is triturated with little acetone to give the title compound.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. temperatureAfter cooling to ambient temperature
  4. washthe solution is washed with water, 2 M hydrochloric acid, and 10% aqueous K2CO3 solution
  5. dry with materialThe solution is dried (MgSO4)
  6. customthe solvent is removed
  7. customthe residue is triturated with little acetone

Sources & evidence

ORD record
ord-123156ca3d0a4b24a58bedbbf67eaffb
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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