Water → 2-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetic acid
Reaction equation
[OH-].[Na+].O.[CH2:4]1[CH:9]2[C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=3[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]2[CH2:7][CH2:6][N:5]1[CH2:23][CH2:24][O:25][CH2:26][C:27]([O:29]CC)=[O:28]>C(O)C>[CH2:4]1[CH:9]2[C:10]3[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=3[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]2[CH2:7][CH2:6][N:5]1[CH2:23][CH2:24][O:25][CH2:26][C:27]([OH:29])=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
7 ml of a 10% w/v aqueous solution of sodium hydroxide and 10 ml of water were added to a solution of 3.2 g of ethyl 2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetate (prepared as described in Example 1) dissolved in 20 ml of ethanol. The mixture was then stirred at room temperature for 1 hour, after which it was concentrated to about one half of its original volume by distillation under reduced pressure. The pH of the concentrate was then adjusted to a value of 4.0 by the addition of 10% w/v aqueous hydrochloric acid, and the mixture was extracted with chloroform. Concentration of the extract by evaporation under reduced pressure yielded 2.96 g (a quantitative yield) of the title compound as a foamy substance, which was recrystallized from water to give colorless needles, melting at 135° C. (with decomposition).
Workup
- concentrationafter which it was concentrated to about one half of its original volume by distillation under reduced pressure
- additionThe pH of the concentrate was then adjusted to a value of 4.0 by the addition of 10%
- extractionthe mixture was extracted with chloroform
- extractionConcentration of the extract by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-dd628e1ddd744324b32f04fd26719fae
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05476848
Reaction notes
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