Sodium Bicarbonate → HCID 68418371, compound

HRID 2061211Notes

Reaction equation

HRID 2061211 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][N:19]([C:22](=[O:36])[CH2:23][N:24]([CH2:32][CH:33]([CH3:35])[CH3:34])C(=O)OC(C)(C)C)[CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[ClH:37].O1CCOCC1.C(=O)([O-])O.[Na+]>O1CCOCC1>[ClH:37].[CH:12]1[C:8]2[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6](=[C:16]3[CH2:17][CH2:18][N:19]([C:22](=[O:36])[CH2:23][NH:24][CH2:32][CH:33]([CH3:34])[CH3:35])[CH2:20][CH2:21]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 59853901HCID 59853901, compound

Product 1

HCID 68418371HCID 68418371, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

128.5 mg (0.264 mmol) of t-butyl 2-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-2-oxoethyl(isobutyl)carbamate was dissolved in 1 ml of 1,4-dioxane. 0.5 ml of 4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution, and they were stirred overnight. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After the extraction with ethyl acetate 3 times, the extract was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=89:11 to 65:35). The solvent was evaporated under reduced pressure, and the residue was dissolved in 2 ml of diethyl ether. 4 N hydrochloric acid/ethyl acetate solution was added to the obtained solution. The precipitates thus formed were taken by the filtration and then washed with diethyl ether. After drying under reduced pressure, the title compound was obtained.

Workup

  1. extractionAfter the extraction with ethyl acetate 3 times
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=89:11 to 65:35)
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in 2 ml of diethyl ether
  7. addition4 N hydrochloric acid/ethyl acetate solution was added to the obtained solution
  8. customThe precipitates thus
  9. customformed
  10. filtrationwere taken by the filtration
  11. washwashed with diethyl ether
  12. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-1e78ec1c128e46528fd1cfa3e67ba04d
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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