Hydrochloric Acid → HCID 23152922, compound

HRID 1012295Notes

Reaction equation

HRID 1012295 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C:23](=O)[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.Cl.[OH-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.O>[CH:1]1([C:7]2[C:8]3[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23152439HCID 23152439, compound

Product 1

HCID 23152922HCID 23152922, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 12-cyclohexyl-4-[2-oxo-2-(piperidin-1-yl)ethoxy]-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (254 mg, 0.49 mmol) in tetrahydrofuran (1 ml) was added a solution (1 ml) of 1M BH3 THF complex in tetrahydrofuran, and the mixture was stirred at room temperature for 3 hr. 2N Hydrochloric acid (2 ml) 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, and the reaction mixture was neutralized by adding 2N aqueous sodium hydroxide solution and saturated aqueous sodium hydrogen carbonate solution. Water was added, and the precipitated solid was collected by filtration and washed with water. The obtained solid was dried in vacuo to give methyl 12-cyclohexyl-4-[2-(piperidin-1-yl)ethoxy]-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (240 mg, yield 97%).

Workup

  1. stirringthe mixture was stirred at 70° C. for 4 hr
  2. temperatureto cool to room temperature
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-5f74a2c28efa4acfbcd69382128f6671
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…