Sodium Hydroxide → Bupivacaine (USAN:INN:BAN)

HRID 1886742Notes

Reaction equation

HRID 1886742 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH: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.Cl.[OH-].[Na+]>O>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH: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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 64737Bupivacaine Hydrochloride

Product 1

HCID 2474Bupivacaine (USAN:INN:BAN)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bupivacaine hydrochloride (Sigma-Aldrich Corporation, St. Louis, Mo.) was dissolved in de-ionized (DI) water at a concentration of 40 mg/ml (saturation). A calculated amount of sodium hydroxide (in the form of 1 N solution) was added to the solution and the pH of the final mixtures was adjusted to ten to precipitate the Bupivacaine base. The precipitated product was filtered, and further washed with DI water for at least three times. The precipitated product was dried at ca. 40° C. in vacuum for 24 hours.

Workup

  1. customto precipitate the Bupivacaine base
  2. filtrationThe precipitated product was filtered
  3. washfurther washed with DI water for at least three times
  4. customThe precipitated product was dried at ca. 40° C. in vacuum for 24 hours

Sources & evidence

ORD record
ord-810d63d043b34203ab16d47ebf78540b
Source dataset
uspto-grants-2013_08
Patent number
US08501215B2

Reaction notes

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