Dichloromethane → HCID 22248292, compound

HRID 606260Notes

Reaction equation

HRID 606260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[N:20][C:19]=2[O:24]C)[CH2:13][CH2:12]1)=[O:10].[OH-].[Na+].ClCCl>Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][C:18]2[C:19](=[O:24])[NH:20][N:21]=[CH:22][CH:23]=2)[CH2:15][CH2:16]1)=[O:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 22247854HCID 22247854, compound

Product 1

HCID 22248292HCID 22248292, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

After dissolving 74 mg of 2-(2-fluorophenyl)-1-[1-(3-methoxy-4-pyridazinylmethyl)piperidin-4-yl]ethanone in 2 ml of 5N hydrochloric acid, the mixture was heated to reflux for 4.5 hours. A 5N sodium hydroxide solution was added to the reaction solution for neutralization, and extraction was performed with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, diethyl ether was added to the residue and the mixture was filtered to obtain the title compound (27 mg, 38% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4.5 hours
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, diethyl ether
  6. additionwas added to the residue
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-b595c77a488e4624a0aa7b4896707f2f
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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