Acetic Acid → Aptazapine

HRID 1902201Notes

Reaction equation

HRID 1902201 reaction equation
[CH3:1][N:2]1[CH2:19][C:18](=O)[N:5]2[C:6]3[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=3[CH2:8][N:9]3[CH:13]=[CH:12][CH:11]=[C:10]3[CH:4]2[C:3]1=O.C(O)(=O)C>O1CCCC1.B#B>[CH3:1][N:2]1[CH2:19][CH2:18][N:5]2[C:6]3[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=3[CH2:8][N:9]3[CH:13]=[CH:12][CH:11]=[C:10]3[CH:4]2[CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 128377852-methyl-1,4-dioxo-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 51355Aptazapine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 6328200DiboronSolvent

Procedure

To the solution of 140 mg of 2-methyl-1,4-dioxo-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine in 5 ml of tetrahydrofuran, 2 ml of 1-molar diborane in tetrahydrofuran are added while stirring and cooling in ice. The mixture is allowed to stir at room temperature overnight and is then refluxed for 4 hours. After cooling to room temperature it is combined with 0.5 ml of glacial acetic acid, evaporated and the residue basified with 3 N aqueous sodium hydroxide. The mixture is extracted with methylene chloride, the extract dried, evaporated and the residue dissolved in diethyl ether. The solution is filtered and the filtrate evaporated to yield the 2-methyl-1,3,4,14b-tetrahydro-10H-pyrazino[1,2-a]pyrrolo[2,1-c][1,4]benzodiazepine, which is identical with that obtained according to Example 1; its monomaleate melts at 176°-178°.

Workup

  1. temperaturecooling in ice
  2. stirringto stir at room temperature overnight
  3. temperatureis then refluxed for 4 hours
  4. customevaporated
  5. extractionThe mixture is extracted with methylene chloride
  6. customthe extract dried
  7. customevaporated
  8. dissolutionthe residue dissolved in diethyl ether
  9. filtrationThe solution is filtered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-48c96745aa0e45b5943fbdaa02064084
Source dataset
uspto-grants-1982_12
Patent number
US04362666

Reaction notes

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