Ammonium Chloride → HCID 54084270, compound

HRID 414490Notes

Reaction equation

HRID 414490 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=O)[CH:21]=[CH:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[C:26]=2[O:35][CH3:36])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>CCOCC>[CH:1]([N:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH:21]=[CH:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[C:26]=2[O:35][CH3:36])[CH2:18][CH2:19]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 538213461-Benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoyl)piperazine

Product 1

HCID 54084270HCID 54084270, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 10.0 g (20.1 mmol) of said 1-benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienoyl)piperazine was added 250 ml of dry ether, and the mixture was stirred. After addition of 760 mg (20.1 mmol) of lithium aluminum hydride, the mixture was heated under reflux for 1 hour To the reaction mixture were added a saturated aqueous solution of ammonium chloride followed by extraction with ether. The organic layer was washed with a saturated aqueous 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 9.40 g (19.4 mmol) of 1-benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienyl)piperazine. Spectrophotometric data of the product support the structure (VIII). ##STR8##

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour To the reaction mixture
  3. extractionfollowed by extraction with ether
  4. washThe organic layer was washed with a saturated aqueous 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-e21ed48558864a2090f6ab6be0437efb
Source dataset
uspto-grants-1988_12
Patent number
US04792553

Reaction notes

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