Benzaldehyde → HCID 21537784, compound

HRID 1076646Notes

Reaction equation

HRID 1076646 reaction equation
Cl.[CH:2]1([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C-:22]#[N:23].[K+].[OH-].[Na+]>O.C(OCC)(=O)C>[CH:2]1([N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22]#[N:23])[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 872981-Cyclohexylpiperazine

Product 1

HCID 21537784HCID 21537784, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To concentrated hydrochloric acid (5.9 g) are added N-cyclohexylpiperazine (5.1 g) and then benzaldehyde (3.2 g) under cooling, and to the mixture is added dropwise a solution of potassium cyanide (2.2 g) in water (4 ml) under stirring. The mixture is heated at 90°C for one hour under stirring, by which the mixture is solidified. The reaction mixture is dissolved in ethyl acetate and thereto is added aqueous sodium hydroxide solution to make it alkaline. After the mixture is shaken, the organic layer is separated, washed with water, dried over anhydrous sodium sulfate and then distilled under a reduced pressure to remove the solvent. The residual crystals are washed with petroleum ether, dried and recrystallized from n-hexane to give the desired compound (7.5 g), colorless needles, m.p. 79° - 81°C.

Workup

  1. stirringunder stirring, by which the mixture
  2. stirringAfter the mixture is shaken
  3. customthe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under a reduced pressure
  7. customto remove the solvent
  8. washThe residual crystals are washed with petroleum ether
  9. customdried
  10. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-24a6e1c6e0ac493d89c77d33dfdb8f35
Source dataset
uspto-grants-1976_05
Patent number
US03957788

Reaction notes

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