Hydrochloric Acid → Bupranolol hydrochloride

HRID 1193475Notes

Reaction equation

HRID 1193475 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:24])=[C:12]([O:14][CH2:15][CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=1.[ClH:25].O>C(Cl)(Cl)Cl>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:24])=[C:12]([O:14][CH2:15][CH:16]([OH:23])[CH2:17][NH:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=1.[ClH:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 2475Bupranolol

Product 1

HCID 27072Bupranolol hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

11.0 g (0.016 mole) 1,3-dipalmitin-succinic acid monoester-acylchloride are dissolved in 350 ml chloroform, cooled to 5° and 1.6 g dry pyridine added. Subsequently, a suspension of 6.2 g bupranolol--HCl in dry chloroform is added in drops over one hour at 5°. The reaction mixture is then further processed for 48 hours under reflux and the exclusion of water at room temperature. The chloroform solution is then washed with 0.1N HCl and water, dried over MgSO4 and evaporated. The rubber-like product obtained in this manner is purified by means of column chromatography. The product may optionally be further processed as in Example 1.

Workup

  1. temperaturecooled to 5°
  2. temperatureunder reflux
  3. customat room temperature
  4. washThe chloroform solution is then washed with 0.1N HCl and water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe rubber-like product obtained in this manner
  8. customis purified by means of column chromatography

Sources & evidence

ORD record
ord-da5df74b873c453eaa6d6f2f887f8b9a
Source dataset
uspto-grants-1989_03
Patent number
US04810697

Reaction notes

Loading…