Maleic Acid → HCID 5384562, compound

HRID 1730103Notes

Reaction equation

HRID 1730103 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[CH2:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[CH2:6]1.[H][H].[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28]>[Pd].C(O)C>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28].[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]([CH3:16])[C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=2[CH2:6]1

Participants

6

Reactant 3

HCID 444266Maleic AcidHCID 547246HCID 547246, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 5384562HCID 5384562, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 5.54 g. (0.02 mole) 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cycloheptene and 0.6 g 5% palladium on carbon in 60 ml. ethanol is hydrogenated at atmospheric pressure and room temperature. The hydrogenation is stopped after 1 equivalent of hydrogen is absorbed, the catalyst is removed by filtration and the filtrate concentrated to a small volume in vacuo. The concentrated filtrate is treated with 2.32 g. (0.02 mole) maleic acid in ethanol and the resulting solid is filtered and washed with cold ethanol to give 10,11-dihydro-10-(2-dimethylaminoethyl)-5-methyl-5H-dibenzo[a,d]cycloheptene maleate, m.p. 120°-122° C.

Workup

  1. additionA mixture of 5.54 g
  2. customis hydrogenated at atmospheric pressure and room temperature
  3. customis absorbed
  4. customthe catalyst is removed by filtration
  5. concentrationthe filtrate concentrated to a small volume in vacuo
  6. additionThe concentrated filtrate is treated with 2.32 g
  7. washwashed with cold ethanol

Sources & evidence

ORD record
ord-589a1c9abd834d1ba4673b6f0cc2cff0
Source dataset
uspto-grants-1976_11
Patent number
US03991102

Reaction notes

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