Hydrochloric Acid → HCID 9933004, compound

HRID 451585Notes

Reaction equation

HRID 451585 reaction equation
[CH:1]1[C:6]([F:7])=[CH:5][C:4]2[CH2:8][CH2:9][CH:10]([CH:12]([OH:29])[CH2:13][NH:14][CH2:15][CH:16]([OH:28])[CH:17]3[O:26][C:25]4[CH:24]=[CH:23][C:22]([F:27])=[CH:21][C:20]=4[CH2:19][CH2:18]3)[O:11][C:3]=2[CH:2]=1.[ClH:30]>C(O)C>[CH:23]1[C:22]([F:27])=[CH:21][C:20]2[CH2:19][CH2:18][CH:17]([CH:16]([OH:28])[CH2:15][NH:14][CH2:13][CH:12]([OH:29])[CH:10]3[O:11][C:3]4[CH:2]=[CH:1][C:6]([F:7])=[CH:5][C:4]=4[CH2:8][CH2:9]3)[O:26][C:25]=2[CH:24]=1.[ClH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71301Nebivolol

Product 1

HCID 9933004HCID 9933004, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Nebivolol free base (3.30 g, 8.70 mmol) is suspended in absolute ethanol (100 mL) and heated to fall until complete dissolution. To this solution, 1.25 M ethanolic HCl (7.5 mL) is added. The obtained solution is concentrated under reduced pressure, until obtaining a 15% concentration of the product. During solvent evaporation, progressive formation of a white precipitate is observed. The solid is filtered by washing with cold absolute ethanol, to obtain 3.10 g of nebivolol hydrochloride salt. The chiral purity of the product and the ratio between the two enantiomers is evaluated by comparison with reference standards, by HPLC with an AKZO NOBEL column, Kromasil 5-AmyCoat, 5 μm, 250 mm×4.6 and a suitable binary gradient.

Workup

  1. temperatureheated
  2. dissolutionto fall until complete dissolution
  3. concentrationThe obtained solution is concentrated under reduced pressure
  4. customuntil obtaining a 15% concentration of the product
  5. customDuring solvent evaporation, progressive formation of a white precipitate
  6. filtrationThe solid is filtered
  7. washby washing with cold absolute ethanol

Sources & evidence

ORD record
ord-527305b698b341f4936fa7e3e7732e29
Source dataset
uspto-grants-2013_07
Patent number
US08487122B2

Reaction notes

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