Acetone → L-ropivacaine hydrochloride monohydrate

HRID 2245612Notes

Reaction equation

HRID 2245612 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].CC(C)=[O:24]>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.[OH2:24].[Cl-:21]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 175805Ropivacaine

Product 1

HCID 53262281L-ropivacaine hydrochloride monohydrateYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 2 g of Ropivacaine base was dissolved in 10 mL of water and 7.3 mL of concentrated hydrochloride acid was added slowly with stirring and 350 mL of acetone was added and kept at about 0° C. for 2 days. The precipitated solid was filtered, washed with acetone, and dried under vacuum at about 35° C. for about 6 hr: 1.8 g; yield 79%; water content of 5.6%.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with acetone
  3. customdried under vacuum at about 35° C. for about 6 hr

Sources & evidence

ORD record
ord-05b0f58d7008469da3ca90a2f5d349f4
Source dataset
uspto-grants-2010_03
Patent number
US07683175B2

Reaction notes

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