HCID 14476373, compound → HCID 14476385, compound

HRID 359123Notes

Reaction equation

HRID 359123 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[CH:24](O)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Zn]>[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 14476373HCID 14476373, compound

Product 1

HCID 14476385HCID 14476385, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

An agitated solution of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-3-hydroxy-1-isoindolinone (11 g) in acetic acid (80 cc) is heated to a temperature close to 60° C. and 11.3 g of powdered zinc is added in small portions in the course of 10 minutes. The suspension obtained is then heated to a temperature close to 120° C. for 5 hours. The suspension is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 80° C. The residue is dissolved in distilled water (250 cc) and the solution is extracted with methylene chloride (4×50 cc). The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The precipitate formed is recrystallized from boiling acetonitrile (25 cc). 6.1 g of 2-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1-isoindolinone are thus obtained, melting at 104° C.

Workup

  1. customclose to 60° C.
  2. customThe suspension obtained
  3. temperatureis then heated to a temperature
  4. customclose to 120° C. for 5 hours
  5. customThe suspension is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 80° C
  6. dissolutionThe residue is dissolved in distilled water (250 cc)
  7. extractionthe solution is extracted with methylene chloride (4×50 cc)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  11. customThe precipitate formed
  12. customis recrystallized

Sources & evidence

ORD record
ord-5240a80b6e5d43f8a79e5c66318f904b
Source dataset
uspto-grants-1991_03
Patent number
US04999355

Reaction notes

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