Isopropylamine → O-Demethylmetoprolol

HRID 845880Notes

Reaction equation

HRID 845880 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:6][CH:5]=1.[CH:15]([NH2:18])([CH3:17])[CH3:16]>>[OH:1][CH2:2][CH2:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]([OH:12])[CH2:11][NH:18][CH:15]([CH3:17])[CH3:16])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 104201452-{4-[(Oxiran-2-yl)methoxy]phenyl}ethan-1-ol

Product 1

HCID 162181O-Demethylmetoprolol

Procedure

10 g of 1-[4-(2-hydroxyethyl)phenoxy]-2,3-epoxypropane produced in Example 1 was refluxed in 50 mL of isopropylamine for 16 hrs. The amine was removed under reduced pressure, the residue dissolved in warm toluene and the toluene removed under reduced pressure. On standing the oil solidified. Yield=12.8 g (98%). After recrystallization in petroleum ether this solid had a melting point of 77°-78° C.

Workup

  1. customThe amine was removed under reduced pressure
  2. dissolutionthe residue dissolved in warm toluene
  3. customthe toluene removed under reduced pressure
  4. customAfter recrystallization in petroleum ether this solid

Sources & evidence

ORD record
ord-0b9a455e6ea34a9e9a13f0b13d1cd086
Source dataset
uspto-grants-1988_07
Patent number
US04760182

Reaction notes

Loading…