Diethyl Ether → HCID 20569893, compound

HRID 1577832Notes

Reaction equation

HRID 1577832 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]([CH2:21][CH:22]([O:24]C(=O)C)[CH3:23])[CH2:17][CH2:16]1)=[N:8][N:7]=[CH:6]2.CCOCC>[OH-].[Na+].C(O)C>[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]([CH2:21][CH:22]([OH:24])[CH3:23])[CH2:17][CH2:16]1)=[N:8][N:7]=[CH:6]2

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 20569892HCID 20569892, compound

Product 1

HCID 20569893HCID 20569893, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

6,7-Dimethoxy-1-[4-(2-acetoxypropyl)piperidino]phthalazine (1 g) was heated at 90° in a mixture of 5 N sodium hydroxide (5 ml) and ethanol (5 ml) for 30 hours. The mixture was then evaporated in vacuo and the residue suspended in water (25 ml) from which it was extracted with chloroform (2×25 ml). The combined chloroform extracts were washed with water (20 ml) and evaporated in vacuo to give a crude oily product, which solidified on trituration with ether (20 ml). Recrystallization from acetonitrile gave 6,7-dimethoxy-1-[4-(2-hydroxypropyl)piperidino]phthalazine (400 mg), m.p. 154°-6°.

Workup

  1. customThe mixture was then evaporated in vacuo
  2. extractionwas extracted with chloroform (2×25 ml)
  3. washThe combined chloroform extracts were washed with water (20 ml)
  4. customevaporated in vacuo
  5. customto give a crude oily product, which
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-425e2cfce0184b5a8e75220451196eb1
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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