Hydrochloric Acid → HCID 12901730, compound

HRID 1680499Notes

Reaction equation

HRID 1680499 reaction equation
[C:1]1(=O)[CH:6]2[C:7]3[C:12]([C:13](=O)[N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.B.O.Cl>O1CCCC1>[CH2:1]1[CH:6]2[C:7]3[C:12]([CH2:13][N:5]2[CH2:4][CH2:3][NH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6331BoraneHCID 12901715HCID 12901715, compound

Product 1

HCID 12901730HCID 12901730, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Dihydropyrazino[2,1-a]isoindole-1,6(2H,10bH)-dione (described in Example 6, 14 g, 0.0674 mol) is added portionwise to 700 ml of 1 M borane in tetrahydrofuran over a 0.5 hr period and then refluxed with stirring for 18 hr. The reaction is cooled, water is added dropwise until the hydrolysis is complete and then 140 ml of 6 N hydrochloric acid is added cautiously. Most of the tetrahydrofuran is distilled off until the distillation temperature reaches 90° C. Then 6 N sodium hydroxide (140 ml) is added and the solution is extracted with chloroform. The chloroform extract is washed with water, dried and evaporated to give the title compound (10 g), nmr (CDCl3) δ 2.63(s), 2.6-4.3(m) and 7.3(m). The title compound is treated with a solution of hydrogen bromide in diethyl ether to give a solid. The solid is crystallized from ethanol to obtain the hydrobromide salt of the title compound, mp 155°-160° C. The title compound (8.9 g) is dissolved in a solution of ethanol containing maleic acid (6.45 g), charcoal is added and the mixture is filtered. The filtrate is evaporated and the residue is crystallized from ethanol-diethyl ether to obtain the maleate salt of the title compound, mp 133°-136° C., Anal. Calc'd. for C11H14N2.C4H4O4 : C, 62.06%, H, 6.25% N, 9.65% and Found: C, 62.00% H, 6.29% N, 9.70%.

Workup

  1. temperaturerefluxed
  2. temperatureThe reaction is cooled
  3. distillationMost of the tetrahydrofuran is distilled off until the distillation temperature
  4. customreaches 90° C
  5. additionThen 6 N sodium hydroxide (140 ml) is added
  6. extractionthe solution is extracted with chloroform
  7. extractionThe chloroform extract
  8. washis washed with water
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-6c7bda107c8c4283a3b52b57d009a85e
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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