Hydrochloric Acid → Levobunolol Hydrochloride

HRID 22087

Reaction equation

HRID 22087 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][C@H:7]([OH:21])[CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=12)([CH3:4])[CH3:3].[ClH:22]>C(O)C>[CH3:4][C:2]([NH:5][CH2:6][C@H:7]([OH:21])[CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=12)([CH3:1])[CH3:3].[ClH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 39468Levobunolol

Product 1

HCID 5284409Levobunolol HydrochlorideYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the above toluenic solution containing levobunolol as free base, 16 ml ethanol and the stoichiometric amount of hydrogen chloride were added. The stirred mixture was cooled below 10° C. and kept at this temperature for one hour. The precipitated solid was filtered, washed with toluene, recrystallized twice from 43 ml ethanol and dried to give 10.0 g (51% yield) of levobunolol hydrochloride having a rotary power at 25° C. below -19°.

Workup

  1. temperatureThe stirred mixture was cooled below 10° C.
  2. filtrationThe precipitated solid was filtered
  3. washwashed with toluene
  4. customrecrystallized twice from 43 ml ethanol
  5. customdried

Sources & evidence

ORD record
ord-6a3b1f99d2ba4f2d923b4e3351667225
Source dataset
uspto-grants-1995_06
Patent number
US05426227

Linked notes

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