Hydrochloric Acid → 1-Amino-2-[3-(3-hydroxymethylphenoxy)propylamino]-1-cyclobutene-3,4-dione

HRID 1651346Notes

Reaction equation

HRID 1651346 reaction equation
[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])[CH:14]=1.N1CCCCC1.Cl.O>C(O)C.[Pd]>[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8082PiperidineHCID 230519081-Amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione

Product 1

HCID 230519061-Amino-2-[3-(3-hydroxymethylphenoxy)propylamino]-1-cyclobutene-3,4-dioneYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-amino-2-[3-(3-formylphenoxy)propylamino]-1-cyclobutene-3,4-dione (2.09 g, 7.29 mmoles), piperidine (0.8 mL, 690 mg, 8.1 mmoles) and 200 mg of 10% Pd/C in 300 mL of 95% ethanol was shaken on a Parr hydrogenator at 50 psi for 4 hours. To the resultant mixture with stirring was added 8.3 mL of aqueous 1.0N HCl and 25 mL of water. The reaction mixture was filtered through diatomaceous earth and the filtrate was evaporated under reduced pressure. The solid residue was treated with acetone and allowed to stand at 0° C. for 18 hours. The mixture was filtered and the solid dried to give 1.437 g of product containing a small amount of starting aldehyde; mp=207°-212° C.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated under reduced pressure
  3. additionThe solid residue was treated with acetone
  4. waitto stand at 0° C. for 18 hours
  5. filtrationThe mixture was filtered
  6. customthe solid dried

Sources & evidence

ORD record
ord-398904e3aaf54b5f9d006cdb0dbc4cbe
Source dataset
uspto-grants-1990_05
Patent number
US04927968

Reaction notes

Loading…