Oxalic Acid → HCID 86614366, compound

HRID 746920Notes

Reaction equation

HRID 746920 reaction equation
[CH3:1][CH:2]([CH2:4][CH:5]([N:17]([CH3:19])[CH3:18])[C:6]1([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH2:9][CH2:8][CH2:7]1)[CH3:3].[C:20]([OH:25])(=[O:24])[C:21]([OH:23])=[O:22]>CO>[CH3:3][CH:2]([CH2:4][CH:5]([N:17]([CH3:18])[CH3:19])[C:6]1([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH2:7][CH2:8][CH2:9]1)[CH3:1].[C:20]([O-:25])(=[O:24])[C:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 5210Sibutramine2×

Product 1

HCID 86614366HCID 86614366, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

15 g of sibutramine was dissolved in 60 ml of methanol. Oxalic acid (5.07 g) dissolved in 20 ml methanol was slowly added in droplets to the sibutramine solution at room temperature and agitated for 2 hrs. The resulting solution was cooled to 0° C., agitated for about 2 hrs, and filtered to collect deposited crystals. The crystals were washed with 50 ml of isopropyl ether and vacuum-dried at 50° C., thus obtaining 18 g (yield: 89.7%) of a white target compound.

Workup

  1. stirringagitated for about 2 hrs
  2. filtrationfiltered
  3. customto collect
  4. washThe crystals were washed with 50 ml of isopropyl ether
  5. customvacuum-dried at 50° C.

Sources & evidence

ORD record
ord-7986168820f84ab7befdc7cfd767f092
Source dataset
uspto-grants-2008_07
Patent number
US07393977B2

Reaction notes

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