Acetone → L-ropivacaine hydrochloride monohydrate

HRID 2245610Notes

Reaction equation

HRID 2245610 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 180AcetoneHCID 313Hydrochloric AcidHCID 175805Ropivacaine

Product 1

HCID 53262281L-ropivacaine hydrochloride monohydrateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

About 2 g of Ropivacaine base was dissolved in a mixture of 2.6 mL of concentrated hydrochloride acid and 5 mL of water at about 30° C. This mixture was stirred at a temperature of about 50° C. for about 30 min and then hot acetone (100 ml) was added. The mixture was then held at about 0 to 5° C. and stirring continued for about 2 hr. A precipitated solid was filtered, washed with acetone, and then dried under vacuum at about 35° C. for about 6 hr. 2.1 g, yield 93%, water content: 5.5%. All water contents herein are determined by Karl Fisher titration.

Workup

  1. customwas then held at about 0 to 5° C.
  2. stirringstirring
  3. waitcontinued for about 2 hr
  4. filtrationA precipitated solid was filtered
  5. washwashed with acetone
  6. customdried under vacuum at about 35° C. for about 6 hr

Sources & evidence

ORD record
ord-6320b5e179824753a2990fe8a92a3e29
Source dataset
uspto-grants-2010_03
Patent number
US07683175B2

Reaction notes

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