Propranolol Hydrochloride → HCID 53833412, compound

HRID 845723

Reaction equation

HRID 845723 reaction equation
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:3].Cl.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.Cl[C:38]([O:40][CH:41]([Cl:43])[CH3:42])=[O:39]>C(Cl)(Cl)Cl>[Cl:43][CH:41]([O:40][C:38]([N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:39])[CH3:42]

Participants

5

Reactant 3

HCID 62882Propranolol HydrochlorideHCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 53833412HCID 53833412, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of propanolol hydrochloride (3.0 g) in chloroform (100 ml) was mixed with proton sponge® (4.3 g) and cooled in an ice bath. 1-Chloroethyl chloroformate (1.5 g) was added dropwise to the reaction mixture. The suspension dissolved in about 5 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours. The chloroform solution was washed with water, 3N HCl and water successively. The organic layer was dried over Na2SO4 and evaporated to a thick oil weighing 3.6 g. NMR (CDCl3) δ1.25 (6H, d, J=7 Hz, CH(Me)2), 1.8 (3H, d, J=7 Hz, CH3CH), 3.3=3.6 (3H, m, ArOCH2 and CH(Me)2), 4.0-4.6 (3H, m, NCH2 and CHOH), 6.61 (1H, q, J=7 Hz, CH3CH) and 6.7-8.4 (7H, m, aromatic). IR (film) ν3450, 1715, 1583, 1270, 1248, 1108 cm-1.

Workup

  1. temperaturecooled in an ice bath
  2. dissolutionThe suspension dissolved in about 5 minutes
  3. customThe cooling bath was removed
  4. washThe chloroform solution was washed with water, 3N HCl and water successively
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated to a thick oil

Sources & evidence

ORD record
ord-7dc69a75ea4c464c9a630191f4f46948
Source dataset
uspto-grants-1988_07
Patent number
US04760057

Linked notes

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