Hydrochloric Acid → HCID 66795232, compound

HRID 1012296Notes

Reaction equation

HRID 1012296 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:33]=[CH:32][C:31]([C:34]([O:36]C)=[O:35])=[CH:30][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[ClH:40]>O1CCCC1.CO>[ClH:40].[CH:1]1([C:7]2[C:8]3[CH:33]=[CH:32][C:31]([C:34]([OH:36])=[O:35])=[CH:30][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:14]=2[O:13][CH2:12][CH2:11]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23152922HCID 23152922, compound

Product 1

HCID 66795232HCID 66795232, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 12-cyclohexyl-4-[2-(piperidin-1-yl)ethoxy]-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (240 mg, 0.48 mmol) in tetrahydrofuran (4 ml) and methanol (4 ml) was added 4N aqueous sodium hydroxide (2.5 ml), and the mixture was stirred at 60° C. for 2 hr. 2N Hydrochloric acid (5.1 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate:tetrahydrofuran (2:1). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. To a solution of the obtained residue in tetrahydrofuran (1 ml) was added 4N HCl-ethyl acetate solution (2 ml). The solvent was evaporated under reduced pressure, and hexane:ethyl acetate (4:1) solution was added to the obtained residue. The precipitated solid was collected by filtration and washed with hexane:ethyl acetate (4:1) solution. The obtained solid was dried in vacuo to give 12-cyclohexyl-4-[2-(piperidin-1-yl)ethoxy]-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid hydrochloride (160 mg, yield 64%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate:tetrahydrofuran (2:1)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additionTo a solution of the obtained residue in tetrahydrofuran (1 ml) was added 4N HCl-ethyl acetate solution (2 ml)
  7. customThe solvent was evaporated under reduced pressure, and hexane:ethyl acetate (4:1) solution
  8. additionwas added to the obtained residue
  9. filtrationThe precipitated solid was collected by filtration
  10. washwashed with hexane:ethyl acetate (4:1) solution
  11. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-f383f57f91004b58a2262c8f507434cc
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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