Sibutramine → HCID 86614368, compound

HRID 2114156Notes

Reaction equation

HRID 2114156 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].[Br:20]([OH:23])(=[O:22])=[O:21]>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].[Br:20]([O-:23])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 5210SibutramineHCID 24445Bromic acid

Product 1

HCID 86614368HCID 86614368, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Sibutramine (28.0 g, 0.1 mol) was dissolved in 280 ml of ethyl acetate with agitation. After the solution was adjusted to 25° C., 17.2 g of 47% bromic acid was slowly added in droplets to the solution to form crystals. The resulting mixture was agitated at 25° C. for 2 hrs and further agitated at 4° C. for 1 hr. The generated solid was recovered by filtration under pressure, washed with 100 ml of ethyl acetate, and vacuum-dried at 40° C., thus obtaining 33.1 g (yield: 92%) of a target compound.

Workup

  1. customwas adjusted to 25° C.
  2. customto form crystals
  3. stirringfurther agitated at 4° C. for 1 hr
  4. filtrationThe generated solid was recovered by filtration under pressure
  5. washwashed with 100 ml of ethyl acetate
  6. customvacuum-dried at 40° C.

Sources & evidence

ORD record
ord-6e30b0672a884255953422bf51b712f0
Source dataset
uspto-grants-2008_10
Patent number
US07432398B2

Reaction notes

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