Acetone → L-ropivacaine hydrochloride monohydrate

HRID 2245613Notes

Reaction equation

HRID 2245613 reaction equation
[CH3:1][CH2:2][CH2:3][N:4]1[C@H:9]([C:10]([NH:12][C:13]2[C:14]([CH3:20])=[CH:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.CC(C)=[O:23].[ClH:25]>O>[CH3:1][CH2:2][CH2:3][NH+:4]1[C@H:9]([C:10]([NH:12][C:13]2[C:14]([CH3:20])=[CH:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.[OH2:23].[Cl-:25]

Participants

5

Reactant 3

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 175805Ropivacaine

Product 1

HCID 53262281L-ropivacaine hydrochloride monohydrateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 3 g of Ropivacaine base was dissolved in 10 mL of water and to this solution was added 50 mL of hot acetone and conc. Hydrochloride acid was added slowly with stirring until pH reaches 2 and heated to reflux until the solution becomes clear solution. 20 mL of acetone was added and the precipitated solid was filtered, washed with acetone and dried to give L-Ropivacaine hydrochloride monohydrate 2.9 g, yield 82% Water content: 5.6%

Workup

  1. additionwas added slowly
  2. temperatureheated
  3. temperatureto reflux until the solution
  4. filtrationthe precipitated solid was filtered
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-2de48fcf85494882b3f9290ce1bd91eb
Source dataset
uspto-grants-2010_03
Patent number
US07683175B2

Reaction notes

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