Sodium Cyanide → HCID 22907111, compound

HRID 264306Notes

Reaction equation

HRID 264306 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[C-:13]#[N:14].[Na+].[Cl-].[NH4+:17].[OH-].[NH4+]>O>[C:1]([N:6]1[CH2:11][CH2:10][C:9]([NH2:17])([C:13]#[N:14])[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 22907111HCID 22907111, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of N-carboethoxy-4-piperidone (88.6 g, 517.2 mmol), sodium cyanide (30.0 g, 612.1 mmol) in water (54 mL), ammonium chloride (34.0 g, 635.5 mmol) in water (72 mL), and ammonium hydroxide (76 ml) is heated to 60°-65° C. for 5 hours, and then stirred at room temperature overnight. The resulting solid is filtered off, dissolved in methylene chloride, and washed with a small amount of brine. The organic layer is dried (MgSO4), concentrated in vacuo to 1/2 volume, and triturated with hexane. The resulting precipate is collected by filtration and dried under vacuum, to give N-carboethoxy-4-amino-4-cyanopiperidine.

Workup

  1. filtrationThe resulting solid is filtered off
  2. dissolutiondissolved in methylene chloride
  3. washwashed with a small amount of brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated in vacuo to 1/2 volume
  6. customtriturated with hexane
  7. filtrationThe resulting precipate is collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-8054e627170f4c2da78913583a511248
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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