Potassium Hydroxide → HCID 14441411, compound

HRID 1904656Notes

Reaction equation

HRID 1904656 reaction equation
[CH3:1][C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:4][C:5]([CH2:8][CH2:9][C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=O)=[N:6][CH:7]=1.O.NN.[OH-].[K+]>C(O)COCCOCCO>[CH3:1][C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20037604HCID 20037604, compound

Product 1

HCID 14441411HCID 14441411, compound

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
185 °C

Procedure

To a solution of 86 mg of 5-methyl-2-[3-(1-naphthyl)-3-oxopropyl]-4-piperidinopyridine in 2 ml of triethylene glycol was added 48 mg of 100% hydrazine hydrate, and the mixture was heated at 110° to 120° C. for 2 hours. Then, 68 mg of potassium hydroxide was added, and the bath temperature was raised to about 185° C. The mixture was further heated at this temperature for 5 hours. The reaction mixture was poured into ice and extracted with ether. The ether layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with chloroform) to give 5-methyl-2-[3-(1-naphthyl)propyl]-4-piperidinopyridine as an oil. The product was treated witn an ethanol solution of hydrogen chloride, and recrystallized from acetone/ether to give 28 mg (yield 28%) of the captioned compound.

Workup

  1. temperaturethe mixture was heated at 110° to 120° C. for 2 hours
  2. temperatureThe mixture was further heated at this temperature for 5 hours
  3. additionThe reaction mixture was poured into ice
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluted with chloroform)

Sources & evidence

ORD record
ord-8328dca0d75c4b6baea4b05179670e84
Source dataset
uspto-grants-1989_06
Patent number
US04839353

Reaction notes

Loading…