Sodium Cyanide → HCID 22907111, compound

HRID 1720601Notes

Reaction equation

HRID 1720601 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-107837fd1cde4cb88990a200b312c648
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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