Hydrogen chloride-ethyl acetate → HCID 66795186, compound

HRID 1012338Notes

Reaction equation

HRID 1012338 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[C:10]2[C:23]3[O:22][CH2:21][CH2:20][N:19]4[C:15](=[C:16]([CH:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:45].C(OCC)(=O)C>C(Cl)(Cl)Cl>[ClH:45].[ClH:45].[ClH:45].[N:39]1([CH2:38][CH2:37][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:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]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)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 23152802HCID 23152802, compound

Product 1

HCID 66795186HCID 66795186, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate
  2. additionwas added
  3. filtrationThe precipitated solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b15ce53e2177443aabf4cccd45784153
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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