Fumaric Acid → HCID 70605269, compound

HRID 2163348Notes

Reaction equation

HRID 2163348 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([CH:11]2[CH2:14][N:13](C(C3C=CC=CC=3)C)[CH2:12]2)[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>[OH-].[OH-].[Pd+2].C(O)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[C:1]1([C:7]([CH:11]2[CH2:14][NH:13][CH2:12]2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 54063020HCID 54063020, compound

Product 1

HCID 70605269HCID 70605269, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 23 g. (0.062 mole) of α,α-diphenyl-α-[1-(1-phenylethyl)-3-azetidinyl]acetamide in 150 ml. of ethanol solution was added 1.5 g. of 10% palladium hydroxide on carbon. The mixture was hydrogenated at 70° C. and an initial pressure of 45 p.s.i. for 18 hours and filtered. The filtrate was concentrated and the residue dissolved in 150 ml. of isopropyl alcohol. To this was added 7.2 g. (0.062 mole) of fumaric acid. The resulting crystals were recrystallized three times from ethanol to give 3 g. (13%) of product melting at 171°-173° C.

Workup

  1. additionTo a suspension of 23 g
  2. customwas hydrogenated at 70° C.
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue dissolved in 150 ml
  6. additionTo this was added 7.2 g
  7. customThe resulting crystals were recrystallized three times from ethanol
  8. customto give 3 g

Sources & evidence

ORD record
ord-ddd4b9e51a70476daee927a76779d8f4
Source dataset
uspto-grants-1979_01
Patent number
US04133881

Reaction notes

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