Isopropylamine → Befunolol

HRID 1438812Notes

Reaction equation

HRID 1438812 reaction equation
[K].[C:2]([C:5]1[O:6][C:7]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)(=[O:4])[CH3:3].[CH:15]([NH2:18])([CH3:17])[CH3:16].[CH2:19]([CH:21]1[O:23][CH2:22]1)Cl>C(O)C>[C:2]([C:5]1[O:6][C:7]2[C:13]([O:14][CH2:19][CH:21]([OH:23])[CH2:22][NH:18][CH:15]([CH3:17])[CH3:16])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 7835EpichlorohydrinHCID 5953292-Acetyl-7-hydroxybenzofuranHCID 5462222Potassium

Product 1

HCID 2309Befunolol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 214 mg. of potassium salt of 2-acetyl-7-hydroxybenzofuran, 70 mg. of isopropylamine and 0.8 ml. of epichlorohydrin was suspended into 5 ml. of ethanol. After heating the suspension in a sealed tube at 100° C. for 20 hours, the reaction mixture was filtered and then the solvent was evaporated under a reduced pressure. The residue was subjected to thin layer chromatography (solid support: Kieselgel PF254 made by E. Merck, developer: benzene-chloroform-methanol-28 % aqueous ammonia (17:4:3:0.4), eluant: chloroform) for the purification to give 2-acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran having a melting point of 115° C.

Workup

  1. additionA mixture of 214 mg
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was subjected to thin layer chromatography (solid support: Kieselgel PF254 made by E. Merck, developer: benzene-chloroform-methanol-28 % aqueous ammonia (17:4:3:0.4), eluant: chloroform) for the purification

Sources & evidence

ORD record
ord-2f4dc320e8ec472aa9b6bfc8e0bbd185
Source dataset
uspto-grants-1977_11
Patent number
US04056626

Reaction notes

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