Oxalic Acid → HCID 20311714, compound

HRID 867016Notes

Reaction equation

HRID 867016 reaction equation
[Mg].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6](Cl)[CH2:5][CH2:4]1.[Cl-].[NH4+].[C:12]([OH:17])(=[O:16])[C:13]([OH:15])=[O:14]>C(Br)C.O1CCCC1.CCOCC.C(O)(C)C>[C:12]([OH:17])(=[O:16])[C:13]([OH:15])=[O:14].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:5]2[CH:4]=[C:12]([CH3:13])[CH:8]=[CH:7][CH:6]=2)[CH2:5][CH2:4]1

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224Magnesium

Product 1

HCID 20311714HCID 20311714, compound

Reagents, catalysts & solvents 4

HCID 6332Ethyl BromideCatalystHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A few drops of ethyl bromide are added to a stirring suspension, under nitrogen, of 3.2 g of magnesium turnings in 10 ml of tetrahydrofuran. After a reaction begins, 17.7 g of N-methyl-4-chloropiperidine in 50 ml of tetrahydrofuran are added dropwise while maintaining a moderate reflux. After total addition, the reaction mixture is heated at reflux for 1 hour and 15.2 g of 3-tolyinitrile in 10 ml of tetrahydrofuran are slowly added. After this addition is complete the reaction mixture is heated at reflux for an additional 2 hours and then permitted to stir at ambient temperature for 16 hours. The reaction mixture is poured into a solution of 35 g of ammonium chloride in 500 ml of ice-water and heated on a steam bath for 3 hours, cooled and extracted with benzene. The combined benzene extracts are dried and most of the benzene is removed, leaving an orange oil. The oil is dissolved in ether and the oxalate salt is prepared by the addition of a solution of anhydrous oxalic acid in isopropanol. The white oxalate salt is recrystallized twice from ethanol to give the product, mp 183°-185° C., 1-methyl-4-(3-toluyl)piperidine oxalate.

Workup

  1. temperaturewhile maintaining a moderate reflux
  2. additionAfter total addition
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 1 hour
  5. additionAfter this addition
  6. temperatureis heated
  7. temperatureat reflux for an additional 2 hours
  8. temperatureheated on a steam bath for 3 hours
  9. temperaturecooled
  10. extractionextracted with benzene
  11. dry with materialThe combined benzene extracts are dried and most of the benzene
  12. customis removed
  13. customleaving an orange oil
  14. customThe white oxalate salt is recrystallized twice from ethanol

Sources & evidence

ORD record
ord-bcda55ba79ab42c486bbc0b65c0c0fc5
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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