Water → 67469-58-3

HRID 2286358Notes

Reaction equation

HRID 2286358 reaction equation
[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]=[CH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:14][CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:39]1CCCC1.[OH2:44].C([O:47][CH2:48][CH3:49])C>>[C:48]([OH:47])(=[O:39])/[CH:49]=[CH:1]\[C:7]([OH:8])=[O:44].[C:27]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH2:9][CH2:10][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]=[CH:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:14][CH2:13]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 54400511HCID 54400511, compound

Product 1

HCID 7057556767469-58-3

Conditions

Temperature
50 °C

Procedure

A solution of 6 g of 1-[(diphenylmethoxy)acetyl]-4-(3-phenyl-2-propenyl) piperazine in 100 ml of anhydrous diethyl ether was added dropwise at room temperature to a mixture of 1 g of lithium aluminum hydride and 150 ml of anhydrous diethyl ether. The mixture was refluxed for one hour and then cooled and decomposed by a mixture of tetrahydrofuran and water. The organic layer was separated off and the solvents were distilled off. The residue was dissolved in diethyl ether. The solution was dried over sodium sulphate, after which maleic acid in diethyl ether was added until the liquid was acidic. The precipitate was filtered off and crystallized from a mixture of methanol and dimethylformamide. The thin layer chromatogram revealed an impurity. The substance was therefore stirred with water of 50° C. and then filtered off and dried in vacuo at 60° C. 1-[2-(Diphenylmethoxy)ethyl]-4-(3-phenyl-2-propenyl) piperazine maleate (1:1) was obtained. Melting point 191° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. temperaturecooled
  3. customThe organic layer was separated off
  4. distillationthe solvents were distilled off
  5. dissolutionThe residue was dissolved in diethyl ether
  6. dry with materialThe solution was dried over sodium sulphate
  7. additionafter which maleic acid in diethyl ether was added until the liquid
  8. filtrationThe precipitate was filtered off
  9. customcrystallized from a mixture of methanol and dimethylformamide
  10. filtrationfiltered off
  11. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-74099b744a394d7195349c7022462a41
Source dataset
uspto-grants-1981_05
Patent number
US04265894

Reaction notes

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