Triethylamine → HCID 86745976, compound

HRID 654084Notes

Reaction equation

HRID 654084 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[O:11][CH2:12][CH:13]1[CH2:16][N:15](C(C2C=CC=CC=2)C)[CH2:14]1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>C(O)C.[Pd]>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[CH3:8][C:9]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:10]=1[O:11][CH2:12][CH:13]1[CH2:16][NH:15][CH2:14]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 444266Maleic AcidHCID 19888358HCID 19888358, compound

Product 1

HCID 86745976HCID 86745976, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Triethylamine (2 mL) was added to a solution of 3-[(2,6-dimethylphenoxy)methyl]-1-(1-phenylethyl)azetidine (6.01 g, 21.3 mmol) in absolute ethanol (100 mL). The solution was hydrogenated on a Parr apparatus with approximately 1 g of 10% Pd on carbon as a catalyst at 55° C. and 60 psi (initial pressure) overnight. The mixture was cooled, filtered, and concentrated in vacuo. The residue was dissolved in 2-propanol and added to a solution of maleic acid (2.1 g, 18 mmol). The solid which formed was collected by filtration and recrystallized from 2-propanol to give 5.3 g (81%) of white solid; mp 150°-151.5° C.

Workup

  1. customovernight
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 2-propanol
  6. customThe solid which formed
  7. filtrationwas collected by filtration
  8. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-93920513f28f4288a084599bacf25f9c
Source dataset
uspto-grants-1992_07
Patent number
US05130309

Reaction notes

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