Sodium Hydroxide → HCID 86746671, compound

HRID 1614643Notes

Reaction equation

HRID 1614643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:20][CH2:19]2)=[N:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44]>C1COCC1.CO.CCOCC.C(Cl)Cl.O>[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]/[C:43]([OH:45])=[O:44].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:20][CH2:19]2)[NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 19771943HCID 19771943, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86746671HCID 86746671, compoundYield 73.8%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7.85 g (0.0188 mol) of α-(4-fluorophenyl)-N-[(4-fluorophenyl)methyl]-1-(2-phenylethyl)-4-piperidinemethanimine and 1.30 g (0.034 mol) of lithium aluminum hydride in 200 mL of dry THF (distilled from sodium-benzophenone ketyl) and under an atmosphere of nitrogen was stirred at room temp for 14 h. A solution of 5% NaOH was added dropwise to the mixture and 20 mL of water was added. Methylene chloride was added and the mixture was filtered through Celite. The filtrate was extracted with water and was dried (Na2SO4). The solvent was removed in vacuo to give an oil. This was dissolved in methanol, treated with 4.41 g (0.038 mol) of fumaric acid, and anhydrous ether was added. A precipitate formed to give 7.45 g (65.4%) of the title compound as a white solid, mp 177°-179° C.

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered through Celite
  3. extractionThe filtrate was extracted with water
  4. dry with materialwas dried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customto give an oil
  7. additionwas added
  8. customA precipitate formed

Sources & evidence

ORD record
ord-9cebee5b653a4669afa16c8ba02e36f1
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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