Ammonium Chloride → 1-(4,4'-Difluorobenzhydryl)-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienyl)piperazine

HRID 414492Notes

Reaction equation

HRID 414492 reaction equation
[F:1][C:2]1[CH:39]=[CH:38][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])=[C:27]([O:33][CH3:34])[C:26]=3[O:35][CH3:36])[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+].C(Cl)(Cl)Cl.CO>CCOCC>[F:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]([N:14]2[CH2:15][CH2:16][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])=[C:27]([O:33][CH3:34])[C:26]=3[O:35][CH3:36])[CH2:18][CH2:19]2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:39][CH:38]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21584188Chloroform methanolHCID 542410311-(4,4'-Difluorobenzhydryl)-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoyl)piperazine

Product 1

HCID 537259011-(4,4'-Difluorobenzhydryl)-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienyl)piperazineYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10.6 g (20 mmol) of said 1-(4,4' difluorobenzhydryl)-4-(5-(2,3,4-trimethoxyphenyl)-2,4,-pentadienoyl)piperazine was dissolved in 250 ml of dry ether. After addition of 760 mg (20.1 mmol) of lithium aluminum hydride, the mixture was heated under reflux for 1 hour. The reaction mixture, after addition of saturated aqueous solution of ammonium chloride, was extracted with ether. The organic layer was then 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 to give 9.8 g (19 mmol) of 1-(4,4'-difluorobenzhydryl)-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienyl)piperazine from eluates of chloroform-methanol (40:1). Spectrophotometric data of the product support the structure (IX). ##STR9##

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionwas extracted with ether
  4. washThe organic layer was then 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

Sources & evidence

ORD record
ord-4017695b9bad4274a2691212513ebf29
Source dataset
uspto-grants-1988_12
Patent number
US04792553

Reaction notes

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