Hydrochloric Acid → HCID 20569923, compound

HRID 1577830Notes

Reaction equation

HRID 1577830 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([N:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)=[N:8][N:7]=[CH:6]2.[CH2:22]([N:25]=[C:26]=[O:27])[CH2:23][CH3:24].C(N(CC)CC)C.[ClH:35]>C(Cl)(Cl)Cl.C(OCC)(=O)C.CCOCC.O>[ClH:35].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([N:15]1[CH2:16][CH2:17][CH:18]([O:21][C:26](=[O:27])[NH:25][CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20]1)=[N:8][N:7]=[CH:6]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 205698911-(6,7-Dimethoxy-1-phthalazinyl)-4-piperidinol

Product 1

HCID 20569923HCID 20569923, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

6,7-Dimethoxy-1-[4-hydroxypiperidino]phthalazine (0.81 g), n-propyl isocyanate (0.83 g), triethylamine (0.4 ml) and dry chloroform (20 ml) were heated together under reflux for 10 hours. The mixture was then cooled, treated with water (15 ml) and separated. The chloroform layer was shaken with 1 N sodium hydroxide (10 ml), dried (MgSO4) and evaporated in vacuo to give a yellow oil. The oil was dissolved in the minimum volume of chloroform and chromatographed on silica (bed size 3×27 cm). Elution was commenced with chloroform containing gradually increasing amounts of methanol (up to 10%). The first 800 mls of eluant were discarded then 14×70 ml fractions were collected. Appropriate fractions were selected by thin layer chromatography, combined and evaporated in vacuo to give a yellow oil. This oil was dissolved in the minimum volume of ethyl acetate, diluted with ether (30 ml), and acidified to pH 3 with saturated hydrogen chloride. The precipitated solid was collected and recrystallized from acetonitrile to give 6,7-dimethoxy-1-[4-(N-n-propylcarbamoyloxy)piperidino]phthalazine hydrochloride (0.32 g), m.p. 175°-180°.

Workup

  1. temperatureunder reflux for 10 hours
  2. temperatureThe mixture was then cooled
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto give a yellow oil
  7. customchromatographed on silica (bed size 3×27 cm)
  8. washElution
  9. custom14×70 ml fractions were collected
  10. customevaporated in vacuo
  11. customto give a yellow oil
  12. customThe precipitated solid was collected
  13. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-c4ff75b105a5490abc7946f69513fc95
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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