Methanol → HCID 20569921, compound

HRID 1577835Notes

Reaction equation

HRID 1577835 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][C:18](=O)[CH2:17][CH2:16]1)=[N:8][N:7]=[CH:6]2.Cl.CN.[OH-:25].[K+].[C:27]([BH3-])#[N:28].[Na+].C[OH:32]>>[C:12]([OH:13])(=[O:32])[C:3]([OH:25])=[O:2].[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]([NH:28][CH3:27])[CH2:17][CH2:16]1)=[N:8][N:7]=[CH:6]2

Participants

6

Reactant 5

HCID 887Methanol2×HCID 14797Potassium Hydroxide2×HCID 5003444Sodium cyanoborohydride2×HCID 6364545Methylamine hydrochlorideHCID 20569913HCID 20569913, compound

Product 1

HCID 20569921HCID 20569921, compound

Procedure

To 6,7-Dimethoxy-1-(4-oxopiperidino)phthalazine (11 g), methylamine hydrochloride (4.7 g) and potassium hydroxide flakes (1.1 g) in a methanol (200 ml) suspension was added sodium cyanoborohydride (1 g) in methanol (20 ml). The resulting mixture was stirred for 20 hours, after which a further portion of sodium cyanoborohydride (0.2 g) was added. After stirring for an additional 4 hours the mixture was treated with potassium hydroxide flakes (4 g) and evaporated in vacuo. The residue was partitioned between methylenechloride-2 N NaOH (20:10 ml), and the methylene chloride layer was washed with brine, dried (Na2CO3) and evaporated. The crude product was dissolved in the minimum quantity of methyl alcohol and treated with saturated methanolic oxalic acid to precipitate the oxalate salt. Recrystallization from methanol gave 6,7-dimethoxy-1-[4-(N-methylamino)piperidino]phthalazine oxalate (9 g).

Workup

  1. stirringAfter stirring for an additional 4 hours the mixture
  2. customevaporated in vacuo
  3. customThe residue was partitioned between methylenechloride-2 N NaOH (20:10 ml)
  4. washthe methylene chloride layer was washed with brine
  5. dry with materialdried (Na2CO3)
  6. customevaporated
  7. dissolutionThe crude product was dissolved in the minimum quantity of methyl alcohol
  8. additiontreated with saturated methanolic oxalic acid
  9. customto precipitate the oxalate salt
  10. customRecrystallization from methanol

Sources & evidence

ORD record
ord-285c988977334a04ab1a6d96389b94b6
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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