Ammonia → HCID 16792694, compound

HRID 1444586Notes

Reaction equation

HRID 1444586 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].[Cl-].[NH4+:11].[C-:12]#[N:13].[Na+].N>CO.O>[NH2:11][C:6]1([C:12]#[N:13])[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 771591-Ethylpiperidin-4-one

Product 1

HCID 16792694HCID 16792694, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-4-piperidone (13.2 ml, 100 mmol), ammonium chloride (21.4 g, 400 mmol), sodium cyanide (19.6 g, 400 (mmol) and water (550 ml) was stirred at room temperature for 48 h. The pH of the reaction mixture was adjusted to 10.1 and the product was extracted with ethyl acetate. The organic extracts were washed with brine and dried over magnesium sulfate. Rotary evaporation of the solvent gave a mixture of 4-amino-4-cyano-1-ethyl piperazine and 4-hydroxy-4-cyano-1-ethyl piperazine (7.67 g). This mixture of products was treated with 7 M ammonia in methanol (20 ml) and allowed to stand at room temperature for 24 h. The methanol and excess ammonia were removed in vacuo and the residue was cooled to give 4-amino-4-cyano-1-ethylpiperidine as a crystalline solid (7.762 g).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customRotary evaporation of the solvent
  5. customgave
  6. additionThis mixture of products
  7. waitto stand at room temperature for 24 h
  8. customThe methanol and excess ammonia were removed in vacuo
  9. temperaturethe residue was cooled

Sources & evidence

ORD record
ord-b76611ae0dbe4f0582b971eb5dee7365
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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