Dichloromethane → N-(6-Cyanohexanoyl)glycine, ethyl ester

HRID 3335

Reaction equation

HRID 3335 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:8].[C-:16]#[N:17].[K+].ClCCl>C(O)C>[C:16]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:8])#[N:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 86154941N-(6-bromohexanoyl)-glycine, ethyl ester

Product 1

HCID 85707690N-(6-Cyanohexanoyl)glycine, ethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.73 g (84.7·10-3 mol) of N-(6-bromohexanoyl)-glycine, ethyl ester are dissolved in 200 ml of ethanol, and 6.5 g (0.1 mol) of powdered potassium cyanide are added. The reaction mixture is brought to the reflux point and stirred under reflux for 15 hours. After concentration of the mixture under reduced pressure, the residue is taken up with dichloromethane and the organic phase is washed with aqueous sodium chloride solution. The organic phase is dried and concentrated under reduced pressure to give 19 g of the expected product (yield=99%).

Workup

  1. temperatureunder reflux for 15 hours
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. customThe organic phase is dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0e0f1638dcd40c780aa7d8ec6375945
Source dataset
uspto-grants-1998_03
Patent number
US05733928

Linked notes

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