Triethylamine → 6,7-Dimethoxy-1-(3-hydroxymethylpiperidino)phthalazine

HRID 1164507Notes

Reaction equation

HRID 1164507 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[N:4][N:3]=1.[OH:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1.C(N(CC)CC)C>C(O)CC(C)C>[CH3:15][O:14][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[O:12][CH3:13])[C:2]([N:20]1[CH2:21][CH2:22][CH2:23][CH:18]([CH2:17][OH:16])[CH2:19]1)=[N:3][N:4]=[CH:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107308Piperidin-3-ylmethanolHCID 205111771-Chloro-6,7-dimethoxyphthalazine

Product 1

HCID 205112256,7-Dimethoxy-1-(3-hydroxymethylpiperidino)phthalazineYield 60.2%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

1-Chloro-6,7-dimethoxy phthalazine (2.25 g.), 3-hydroxymethylpiperidine (1.72 g.) and triethylamine (1.3 ml.) in iso-amyl alcohol (60 ml.) were heated at 95° C. for 42 hours. The cooled reaction mixture was then filtered and the filtrate was taken to dryness in vacuo. The residue was dissolved in water (100 ml.), 5 N sodium hydroxide solution was added to give a pH of 11 and the basic mixture was then extracted with chloroform (2×100 ml.). The chloroform extracts were combined, dried (MgSO4) and concentrated in vacuo to give a brown oil, which was triturated with ether (50 ml.) and filtered. The resultant solid was crystallized twice from acetonitrile, yielding 6,7-dimethoxy-1-(3-hydroxymethylpiperidino)phthalazine (1.83 g.), m.p. 162°-165° C.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas then filtered
  3. dissolutionThe residue was dissolved in water (100 ml.)
  4. addition5 N sodium hydroxide solution was added
  5. customto give a pH of 11
  6. extractionthe basic mixture was then extracted with chloroform (2×100 ml.)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a brown oil, which
  10. customwas triturated with ether (50 ml.)
  11. filtrationfiltered
  12. customThe resultant solid was crystallized twice from acetonitrile

Sources & evidence

ORD record
ord-5512212279db4f2db5e13bf7d5899dda
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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