Ammonium Chloride → 1-(4,4'-Difluorobenzhydryl)-4-(5-(2,4-dimethoxyphenyl)-2,4-pentadienyl)piperazine

HRID 414488Notes

Reaction equation

HRID 414488 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH:6]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=O)[CH:21]=[CH:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][CH3:34])[CH2:16][CH2:15]2)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH:21]=[CH:22][CH:23]=[CH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][CH3:34])[CH2:16][CH2:15]2)[C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 542344241-(4,4'-Difluorobenzhydryl)-4-(5-(2,4-dimethoxyphenyl)-2,4-pentadienoyl)piperazine

Product 1

HCID 542067791-(4,4'-Difluorobenzhydryl)-4-(5-(2,4-dimethoxyphenyl)-2,4-pentadienyl)piperazineYield 84.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 11.6 g (23.0 mmol) of said 1-(4,4'-difluorobenzhydryl)-4-(5-(2,4-dimethoxyphenyl)-2,4-pentadienoyl)piperazine was added 250 ml of dry ether, and the mixture was stirred. After slow addition of 870 mg (23.0 mmol) of lithium aluminum hydride, the mixture was heated for 1 hour under reflux. To the reaction mixture was added saturated aqueous solution of ammonium chloride, and the mixture was extracted with ether. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. There was obtained a residue, which was subjected to column chromatography on silica gel and eluted with chloroform-methanol (40:1) to give 9.50 g (19.4 mmol) of 1-(4,4'-difluorobenzhydryl)-4-(5-(2,4-dimethoxyphenyl)-2,4-pentadienyl)piperazine. Spectrophotometric data of the product support the structure (VII). ##STR7##

Workup

  1. temperaturethe mixture was heated for 1 hour
  2. temperatureunder reflux
  3. extractionthe mixture was extracted with ether
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThere was obtained a residue, which
  8. washeluted with chloroform-methanol (40:1)

Sources & evidence

ORD record
ord-b57b58fe455b4f8c9a3981df876f4dc9
Source dataset
uspto-grants-1988_12
Patent number
US04792553

Reaction notes

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