Fumaric Acid → HCID 3061539, compound

HRID 848168Notes

Reaction equation

HRID 848168 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:18])[CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)/C=C/C(O)=O.C([O-])(=O)/C=C/C([O-])=O>O1CCCC1.C(O)(C)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:18])[CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 444972Fumaric AcidHCID 3059028HCID 3059028, compoundHCID 5460307FumarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 3061539HCID 3061539, compoundYield 75.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 10.2 g of 1-(4-methoxyphenyl) 3-(4-piperidyl) 1-propanone in 130 ml of dry tetrahydrofurane, maintained at 5° C. and under a nitrogen atmosphere, 2.8 g of lithium aluminum hydride are added in small portions. When the addition is complete, the reaction mixture is heated to 60° C. over five hours, then cooled to 0° C. Then, while maintaining this temperature, 25.2 ml of water are added very slowly. The mineral products are filtered and washed twice with 50 ml of hot methylenechloride. The collected organic solutions are concentrated by evaporation of the solvent. The oil obtained is dissolved in 150 ml of isopropanol and treated with 7.4 g of fumaric acid. In this manner, 7.8 g of 1-(4-methoxyphenyl) 3-(4-piperidyl) 1-propanol in the form of its fumarate are obtained.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture is heated to 60° C. over five hours
  3. temperaturecooled to 0° C
  4. additionare added very slowly
  5. filtrationThe mineral products are filtered
  6. washwashed twice with 50 ml of hot methylenechloride
  7. concentrationThe collected organic solutions are concentrated by evaporation of the solvent
  8. customThe oil obtained

Sources & evidence

ORD record
ord-57cbfb725d784eb6803edd7df6815bb6
Source dataset
uspto-grants-1981_10
Patent number
US04294841

Reaction notes

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