Dichloromethane → 2-Oxopiperidine-1-carbonitrile

HRID 851312Notes

Reaction equation

HRID 851312 reaction equation
[OH-].[Na+].[N:3]#[C:4][NH2:5].Cl[CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].C(Cl)Cl>O>[C:4]([N:5]1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1=[O:12])#[N:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9864Cyanamide2×HCID 14798Sodium HydroxideHCID 740895-Chlorovaleryl chloride

Product 1

HCID 205021192-Oxopiperidine-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

59.4 g (1.484 mols) of sodium hydroxide are dissolved in 370 ml of water, and 13.2 g (0.742 mol) of cyanamide are added in portions to the solution, after cooling to 0° C. 115.0 g (0.742 mol) of δ-chlorovaleric acid chloride are added dropwise to the clear and colourless cyanamide solution, in the course of one hour, at 0° to 8° C.; a strongly exothermic reaction is observed during this dropwise addition and the mixture must therefore be cooled intensively. After the dropwise addition has ended, the mixture is stirred for a further hour at 0° C. 740 ml of methylene chloride are then added and the reaction mixture is warmed at the reflux temperature (40° C.) for one hour. The two phases are separated in a separating funnel. The aqueous phase is extracted again with 740 ml of methylene chloride.

Workup

  1. customin the course of one hour
  2. customat 0° to 8° C.
  3. customa strongly exothermic reaction
  4. additionis observed during this dropwise addition
  5. temperaturethe mixture must therefore be cooled intensively
  6. additionAfter the dropwise addition
  7. temperaturethe reaction mixture is warmed at the reflux temperature (40° C.) for one hour
  8. customThe two phases are separated in a separating funnel
  9. extractionThe aqueous phase is extracted again with 740 ml of methylene chloride

Sources & evidence

ORD record
ord-070f0c5a298d42b7b6a77b3ad9883713
Source dataset
uspto-grants-1983_05
Patent number
US04384084

Reaction notes

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