Oxalyl chloride → HCID 22038368, compound

HRID 1790438Notes

Reaction equation

HRID 1790438 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](Cl)(=[O:27])[C:24](Cl)=[O:25].C(=O)(O)[O-].[Na+]>CCOCC>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15]3[C:20](=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[C:24](=[O:25])[C:23]2=[O:27])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 4003856HCID 4003856, compound

Product 1

HCID 22038368HCID 22038368, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Benzyl-4-(3-methoxyphenyl)aminopiperidine (1.88 g) synthesized in accordance with the method of Referential Example 1 of JP-B 40-6347 was dissolved in ether (38 ml). Into the resultant solution was added dropwise oxalyl chlori de (1.62 g) over 30 min at room temperature followed by heating under reflux for 3.5 hr. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. Into a suspension of aluminum chloride (5.9 g) in methylene chloride (20 ml) was added dropwise a solution of the resulting residue in methylene chloride (100 ml) at 0° C. over 30 min. After the completion of the addition, the resultant mixture was stirred at room temperature for additional 1.5 hr. After the completion of the reaction, the reaction solution was poured into ice and neutralized by adding an aqueous solution of sodium bicarbonate thereto. The resulting precipitate was filtered off and the filtrate was extracted with methylene chloride. After removing the solvent, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give 1-(1-benzylpiperidin-4-yl)-6-methoxyindoline-2,3-dione (1.63 g) (yield: 73%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3.5 hr
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additionInto a suspension of aluminum chloride (5.9 g) in methylene chloride (20 ml)
  5. additionwas added dropwise a solution of the resulting residue in methylene chloride (100 ml) at 0° C. over 30 min
  6. additionAfter the completion of the addition
  7. customAfter the completion of the reaction
  8. additionthe reaction solution was poured into ice
  9. filtrationThe resulting precipitate was filtered off
  10. extractionthe filtrate was extracted with methylene chloride
  11. customAfter removing the solvent
  12. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-e7d4cd65b46a418e97851547d9f306ea
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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