Potassium Hydroxide → HCID 10710035, compound

HRID 361807Notes

Reaction equation

HRID 361807 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:24])[C:15]2[C:20]([C:21](=O)[CH3:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[OH-].[K+]>C(O)COCCOCCO>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH3:24])[C:15]2[C:20]([CH2:21][CH3:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 10567950HCID 10567950, compound

Product 1

HCID 10710035HCID 10710035, compound

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Procedure

A mixture of 1-benzyl-4-(N-methyl-N-(3-acetyl-2-pyridyl)amino)piperidine (XXXIV, EXAMPLE 43, 260 mg), hydrazine monohydrate (0.78 ml) and powdered potassium hydroxide (0.90 g) in triethylene glycol (16 ml) is stirred at 120° for 2 hrs. The condenser is removed, the mixture is heated up to approximately 185°-190°, the condenser is replaced, and the mixture is stirred at 190° for 3 hrs. After cooling to 20°-25°, the mixture is added to water (50 ml) and extracted with methylene chloride (2×50 ml), and the organic phase is washed with water (20 ml) and saline (20 ml), dried over sodium sulfate, concentrated under reduced pressure and chromatographed (silica gel, 70-230 mesh, 25 g; eluting with a gradient of ethyl acetate/hexane (25/75→50/50)) to give the title compound, NMR (CDCl3, 400 MHz) 8.16, 7.46, 7.31, 7.26, 6.88, 3.50, 3.15, 2.92, 2.73, 2.63, 2.00, 1.82, 1.73 and 1.23δ.

Workup

  1. customThe condenser is removed
  2. temperaturethe mixture is heated up to approximately 185°-190°
  3. stirringthe mixture is stirred at 190° for 3 hrs
  4. temperatureAfter cooling to 20°-25°
  5. additionthe mixture is added to water (50 ml)
  6. extractionextracted with methylene chloride (2×50 ml)
  7. washthe organic phase is washed with water (20 ml) and saline (20 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed (silica gel, 70-230 mesh, 25 g
  11. washeluting with a gradient of ethyl acetate/hexane (25/75→50/50))

Sources & evidence

ORD record
ord-f89fa43f701b4ae9baa13a5648981b72
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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