Hydrochloric Acid → L-ropivacaine hydrochloride monohydrate

HRID 2245611Notes

Reaction equation

HRID 2245611 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.[ClH:21]>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.[OH2:11].[Cl-:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 175805Ropivacaine

Product 1

HCID 53262281L-ropivacaine hydrochloride monohydrateYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

About 2 g of Ropivacaine base was dissolved in a mixture of 2.6 mL of concentrated hydrochloride acid and 40 mL of water. The solution was heated to about 85° C. and stirred for about 30 min to get a clear solution and cooled to about 5° C. and continued stirring for about 2 hr. A precipitated solid was recovered and filtered, then washed with acetone and dried under vacuum at about 35° C. for about 6 hr. Results: wt 2.0 g, yield 88.5 %; water content: 5.5%. The x-ray diffraction pattern of the material obtained is shown in FIG. 1.

Workup

  1. customto get a clear solution
  2. temperaturecooled to about 5° C.
  3. stirringcontinued stirring for about 2 hr
  4. customA precipitated solid was recovered
  5. filtrationfiltered
  6. washwashed with acetone
  7. customdried under vacuum at about 35° C. for about 6 hr
  8. customResults
  9. customThe x-ray diffraction pattern of the material obtained

Sources & evidence

ORD record
ord-6247c7d37ba04f85ac086e9e052e7ed4
Source dataset
uspto-grants-2010_03
Patent number
US07683175B2

Reaction notes

Loading…