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

HRID 1604716Notes

Reaction equation

HRID 1604716 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.C([C@H]([C@@H](C([O-])=O)O)O)([O-])=O.[ClH:32]>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:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86754876Levobupivacaine (S,S)-tartrate

Product 1

HCID 1179652-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride (1:1), (2S)-Yield 97.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

Levobupivacaine (S,S)-tartrate (50 g, 0.069 mol) was suspended in isopropanol (150 ml) and heated to 50° C. Hydrogen chloride (5 g, 0.14 mol) gas was introduced. The temperature rose to 65° C. and the solids dissolved. The mixture was heated to 80° C. to ensure complete dissolution. The mixture was cooled to 5° C. and a solid crystallised. The solid was filtered off and washed with isopropanol (2×50 ml) and dried in vacuo to give levobupivacaine hydrochloride (21.9 g, 40%).

Workup

  1. customrose to 65° C.
  2. dissolutionthe solids dissolved
  3. temperatureThe mixture was heated to 80° C.
  4. dissolutiondissolution
  5. temperatureThe mixture was cooled to 5° C.
  6. customa solid crystallised
  7. filtrationThe solid was filtered off
  8. washwashed with isopropanol (2×50 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-834652c3929d40cb9ff594ee948ebf53
Source dataset
uspto-grants-1999_11
Patent number
US05994548

Reaction notes

Loading…