Dichloromethane → HCID 22248292, compound

HRID 914914Notes

Reaction equation

HRID 914914 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-251a9419f4484b5995908f64b1913fc8
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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