Hydrochloric Acid → HCID 23152802, compound

HRID 1012337Notes

Reaction equation

HRID 1012337 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)[C:10]2[C:23]3[O:22][CH2:21][CH2:20][N:19]4[C:15](=[C:16]([CH:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[C:17]5[CH:27]=[CH:26][C:25]([C:28]([O:30]C)=[O:29])=[CH:24][C:18]=54)[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1.CO>[N:40]1([CH2:39][CH2:38][N:9]([CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:10]2[C:23]3[O:22][CH2:21][CH2:20][N:19]4[C:15](=[C:16]([CH:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[C:17]5[CH:27]=[CH:26][C:25]([C:28]([OH:30])=[O:29])=[CH:24][C:18]=54)[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23152534HCID 23152534, compound

Product 1

HCID 23152802HCID 23152802, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-{bis[2-(piperidin-1-yl)ethyl]amino}-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (401 mg, 0.65 mmol) in tetrahydrofuran (4.0 ml) and methanol (4.0 ml) was added 4N aqueous sodium hydroxide solution (4.0 ml), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was adjusted to pH 6 with 2N hydrochloric acid, and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The precipitated solid was collected by filtration to give 4-{bis[2-(piperidin-1-yl)ethyl]amino}-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid. To a solution of the obtained 4-{bis[2-(piperidin-1-yl)ethyl]amino}-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid in chloroform was added 4N HCl-ethyl acetate solution (4.0 ml). The reaction mixture was concentrated under reduced pressure and ethyl acetate was added. The precipitated solid was collected by filtration and dried in vacuo to give 4-{bis[2-(piperidin-1-yl)ethyl]amino}-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid trihydrochloride (338 mg, yield 73%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe mixture was concentrated under reduced pressure, and ethyl acetate
  6. additionwas added to the residue
  7. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-690cd261d77148a691a1f4decaa20c25
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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