Hydrochloric Acid → 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride (1:1), (2S)-

HRID 643764Notes

Reaction equation

HRID 643764 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.[ClH:22]>C(O)(C)C>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.[ClH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 92253Levobupivacaine

Product 1

HCID 1179652-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride (1:1), (2S)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

23.3 g of pure levobupivacaine free base were dissolved in 125 mL of hot isopropanol. To this solution was added 8.8 mL of concentrated hydrochloric acid. The solution was cooled to room temperature and kept at a temperature between 4° C. to 6° C. for two hours. The mixture was vacuum filtered and the solids were stirred with 20 mL of acetone. The mixture was filtered and the solid was allowed to dry in an oven yielding 24.2 g of levobupivacaine hydrochloride ee>99.5%, MP=246-250° C., [α]D25=−12 (c=2, H2O).

Workup

  1. filtrationfiltered
  2. filtrationThe mixture was filtered
  3. customto dry in an oven

Sources & evidence

ORD record
ord-176bd8f1de9c41bd95df64371d0d3af0
Source dataset
uspto-grants-2010_04
Patent number
US07700629B2

Reaction notes

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