Sodium Hydroxide → HCID 22914783, compound

HRID 1377572Notes

Reaction equation

HRID 1377572 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]([CH:17]3[CH2:22][CH:21]([CH3:23])[N:20]([CH3:24])[CH:19](C)[CH2:18]3)(O)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:26]=1.[OH-].[Na+]>OS(O)(=O)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:26]=1)[CH2:7][CH2:8][C:9]1[C:10](/[C:15]/2=[C:17]2/[CH2:22][CH:21]([CH3:23])[NH:20][CH2:24][CH:18]/2[CH3:19])=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22914798HCID 22914798, compound

Product 1

HCID 22914783HCID 22914783, compoundYield 6.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 8-chloro-11-(1,2,6-trimethyl-4-piperidinyl)-6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]pyridin-11-ol (5.0 g, 14.1 mmol) in 85% H2SO4 (100 mL) was heated in an oil bath (60°-65° C.) for 3 hours. The reaction was cooled and diluted with water followed by basification with 25% aq. NaOH solution. The crude product was extracted with CH2Cl2, washed with brine, dried (Na2SO4), filtered and solvent removed. Purification and separation of the E and Z isomers via chromatography (2%→5% MeOH saturated with NH3 in CH2Cl2) gave the title compound (300 mg, 6%).

Workup

  1. temperaturewas heated in an oil bath (60°-65° C.) for 3 hours
  2. temperatureThe reaction was cooled
  3. extractionThe crude product was extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent removed
  8. customPurification and separation of the E and Z isomers via chromatography (2%→5% MeOH saturated with NH3 in CH2Cl2)

Sources & evidence

ORD record
ord-a382f950a5b84a3c8e2e06c3fc523b1c
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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