Potassium Cyanide → HCID 18931291, compound

HRID 1599004Notes

Reaction equation

HRID 1599004 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([C:8]2([O:23][CH2:22][CH2:21][O:20]2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[CH:7]=1.[C-:26]#[N:27].[K+].[Cl-].[NH4+:30].[OH-].[NH4+]>CO.O>[NH2:30][C:16]1([C:26]#[N:27])[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8]2([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:24][CH3:25])[O:20][CH2:21][CH2:22][O:23]2)[CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 18931290HCID 18931290, compound

Product 1

HCID 18931291HCID 18931291, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-[5-(5-chloro-2-methoxyphenyl)-5,5-ethylenedioxypentyl]-4-piperidone (6.62 g, 18 mmol), potassium cyanide (1.4 g, 35.8 mmol), ammonium chloride (2.46 g, 37 mmol), ammonium hydroxide (14M, 4 mL, 56 mmol), water (25 mL) and methanol (120 mL) was heated 2 hours with stirring at approximately 25° C. and then 5 hours at 60° C. The mixture was concentrated and the residue was dissolved in ethyl acetate. The solution was washed with water (3×) and brine (1×), dried (MgSO4) and concentrated to give 4-amino-1-[5-(5-chloro-2-methoxyphenyl)-5,5-ethylenedioxypentyl]piperidine-4-carbonitrile (5.2 g, 13.1 mmol).

Workup

  1. temperaturewas heated 2 hours
  2. custom5 hours
  3. customat 60° C
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed with water (3×) and brine (1×)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6ec8c95eb68941d7a7bc69262c57e715
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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