Malonic Acid → HCID 86614367, compound

HRID 746921Notes

Reaction equation

HRID 746921 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:26])(=[O:25])[CH2:21][C:22]([OH:24])=[O:23]>C(OCC)(=O)C>[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-:26])(=[O:25])[CH2:21][C:22]([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 5210Sibutramine2×

Product 1

HCID 86614367HCID 86614367, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

15 g of sibutramine was dissolved in 60 ml of ethyl acetate. Malonic acid (5.72 g) dissolved in 20 ml ethyl acetate 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 a deposited crystal. The crystal was washed with 50 ml of isopropyl ether and vacuum-dried at 50° C., thus obtaining 19 g (yield: 92.6%) of a white target compound.

Workup

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

Sources & evidence

ORD record
ord-cefbae68aeb34da7b313290c6ac65641
Source dataset
uspto-grants-2008_07
Patent number
US07393977B2

Reaction notes

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