Piperidine → Piperidine, 1-[2-cyano-1-(cyanoimino)ethyl]-

HRID 437855Notes

Reaction equation

HRID 437855 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([N:9]=[C:10](OCC)[CH2:11][C:12]#[N:13])#[N:8]>CO>[C:7]([N:9]=[C:10]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:11][C:12]#[N:13])#[N:8]

Participants

4

Reactant 2

HCID 8082Piperidine2×HCID 12272864Ethanimidic acid, N,2-dicyano-, ethyl ester

Product 1

HCID 91890Piperidine, 1-[2-cyano-1-(cyanoimino)ethyl]-Yield 101.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Piperidine (25.67 g, 0.0302 m) is added dropwise to an ice-cooled solution of 41.36 g (0.0302 m) of ethyl N, 2-dicyanoacetimidate in 60 ml of methanol. The reaction is heterogeneous initially, but soon becomes homogeneous and yellow. The piperidine is added at a rate that maintains a 25° C. reaction temperature. After fifty minutes, the reaction mixture is partitioned between CH2Cl2 and aqueous saturated NaHCO3. The organic phase is dried over Na2SO4 and concentrated in vacuo to give 54 g of a yellow oil which by tlc appears to be pure product. Nmr confirms the presence of product.

Workup

  1. customthat maintains a 25° C.
  2. customreaction temperature
  3. waitAfter fifty minutes
  4. customthe reaction mixture is partitioned between CH2Cl2 and aqueous saturated NaHCO3
  5. dry with materialThe organic phase is dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3511c2125f404160ab77e98efe7988cc
Source dataset
uspto-grants-1977_06
Patent number
US04032559

Reaction notes

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