Ethanol → Latrepirdine

HRID 2369263Notes

Reaction equation

HRID 2369263 reaction equation
[CH3:1][CH2:2]O.CN1CCC(=N[N:12]([CH2:20][CH2:21][C:22]2[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)CC1>Cl.O.C([O-])([O-])=O.[Na+].[Na+]>[CH3:20][N:12]1[CH2:2][CH2:1][C:15]2[N:12]([CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:14]=2[CH2:13]1

Participants

6

Reactant 2

HCID 702EthanolHCID 49765790HCID 49765790, compound

Product 1

HCID 197033LatrepirdineYield 63%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

Concentrated HCl (6 cm3) was added to EtOH (4 cm3). The crude N′-(1-methyl-piperidin-4-ylidene)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine was dissolved in this ethanolic HCl and heated to 100° C. for 30 minutes. The reaction was then cooled, and diluted with H2O (10 cm3), saturated with Na2CO3, and extracted with CHCl3 (3×50 cm3). The combined extracts were dried (MgSO4) and solvent removed. The residual brown oil was purified by flash column chromatography over SiO2 (10×2 cm) eluting with 1:1 EtOAc/MeOH to provide the desired product as a pale brown powder (612 mg, 63% yield over 3 steps based on last pure starting material (2-methyl-5-(N-nitroso-2-p-tolylaminoethyl)pyridine)).

Workup

  1. temperatureThe reaction was then cooled
  2. extractionextracted with CHCl3 (3×50 cm3)
  3. dry with materialThe combined extracts were dried (MgSO4) and solvent
  4. customremoved
  5. customThe residual brown oil was purified by flash column chromatography over SiO2 (10×2 cm)
  6. washeluting with 1:1 EtOAc/MeOH

Sources & evidence

ORD record
ord-393a4bd3e8ef40878a99c256912ac9c0
Source dataset
uspto-grants-2014_04
Patent number
US08703952B2

Reaction notes

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