Hydroxide → HCID 70022772, compound

HRID 1166602Notes

Reaction equation

HRID 1166602 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:17][CH2:16][C:15]3[N:18]=[CH:19][CH:20]=[CH:21][C:14]=3[C:13](=[CH:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][C:28]([C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)([OH:31])[CH2:27][CH2:26]3)[C:12]=2[CH:39]=1)(=O)C.[OH-].O.C(OCC)(=O)C>C(O)C>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([C:28]2([OH:31])[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH:22]=[C:13]3[C:12]4[CH:39]=[C:8]([O:7][CH2:6][CH2:5][OH:4])[CH:9]=[CH:10][C:11]=4[O:17][CH2:16][C:15]4[N:18]=[CH:19][CH:20]=[CH:21][C:14]3=4)[CH2:30][CH2:29]2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 961HydroxideHCID 962WaterHCID 8857Ethyl AcetateHCID 70021368HCID 70021368, compound

Product 1

HCID 70022772HCID 70022772, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[3-(7-(2-acetoxyethyl)oxy-5,11-pyrido[2,3-c][1]benzoxepin-5-ylidene)propyl]-4-(4-chlorophenyl)piperidin-4-ol (Example 50) (140 mg) in ethanol (5 ml) were added 15% sodiun hydroxide aqueous solution (2 ml) and the mixture was heated to reflux for 1 hour. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with methylene chloride-methanol (10:1) to give the titled compound (120 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customthe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with methylene chloride-methanol (10:1)

Sources & evidence

ORD record
ord-6b90f3a7839e4b5ab2caa0a56bfbee8f
Source dataset
uspto-grants-2003_09
Patent number
US06613905B1

Reaction notes

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