Sulfuric Acid → 1-(3-Bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-4-[(4-piperidinyl)acetyl]piperazine

HRID 47353Notes

Reaction equation

HRID 47353 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([CH2:26][CH:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[O:25])[CH2:20][CH2:19]3)[C:5]2=[N:6][CH:7]=1.OS(O)(=O)=O.[OH-].[Na+]>CO.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:9]=3[CH:8]([N:18]3[CH2:19][CH2:20][N:21]([C:24](=[O:25])[CH2:26][CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH2:22][CH2:23]3)[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 108415231,1-Dimethylethyl 4-[[[4-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-YL)-1-piperazinyl]carbonyl]methyl]-1-piperidinecarboxylate

Product 1

HCID 107682201-(3-Bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-4-[(4-piperidinyl)acetyl]piperazineYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

The title compound from Step A above (4.61 g) (7.5 mmoles) was dissolved in methanol (40 mL) and a 10% (v/v) conc. H2SO4 in dioxane solution (100 mL) was added. The mixture was stirred at 25° C. for 2 h and then basified with conc. aqueous NaOH. The mixture was extracted with dichloromethane and the latter was washed with water, dried over MgSO4, filtered and evaporated to dryness. The product was chromatographed on silica gel using 10% (10% conc. NH4OH in methanol)dichloromethane as the eluant to give the title compound (Yield: 2.86 g; 74%)

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe latter was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe product was chromatographed on silica gel using 10% (10% conc. NH4OH in methanol)dichloromethane as the eluant

Sources & evidence

ORD record
ord-67a6fcbfdb864a4fb2c6c88de14936c7
Source dataset
uspto-grants-2004_03
Patent number
US06699872B2

Reaction notes

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