Hydrochloric Acid → HCID 23152534, compound

HRID 1012336Notes

Reaction equation

HRID 1012336 reaction equation
O=[C:2]([N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[CH2:3][N:4]([CH2:33][C:34]([N:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=O)[C:5]1[C:18]2[O:17][CH2:16][CH2:15][N:14]3[C:10](=[C:11]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:12]4[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:13]=43)[C:9]=2[CH:8]=[CH:7][CH:6]=1.Cl.[OH-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[N:36]1([CH2:34][CH2:33][N:4]([CH2:3][CH2:2][N:42]2[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]2)[C:5]2[C:18]3[O:17][CH2:16][CH2:15][N:14]4[C:10](=[C:11]([CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]5)[C:12]5[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:13]=54)[C:9]=3[CH:8]=[CH:7][CH:6]=2)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23152720HCID 23152720, compound

Product 1

HCID 23152534HCID 23152534, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-{bis[2-oxo-2-(piperidin-1-yl)ethyl]amino}-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (500 mg, 0.78 mmol) in tetrahydrofuran (2.0 ml) was added a solution (5.0 ml) of 1M BH3 THF complex in tetrahydrofuran, and the mixture was stirred at room temperature for 14 hr. 2N Hydrochloric acid was added to the reaction mixture, and the mixture was stirred at 70° C. for 4 hr. The reaction mixture was allowed to cool to room temperature, neutralized with 4N aqueous sodium hydroxide solution and saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol-10:1-5:1) to give 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, yield 84%).

Workup

  1. stirringthe mixture was stirred at 70° C. for 4 hr
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (chloroform:methanol-10:1-5:1)

Sources & evidence

ORD record
ord-b7f9281060ab40c5aa8b4e735afe52e4
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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