Carvedilol → 2-(2-Methoxyphenoxy)ethyl amine

HRID 47919Notes

Reaction equation

HRID 47919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]([OH:30])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[NH:29][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]=12>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]([OH:30])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[NH:29][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]=12.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][NH2:12]

Participants

5

Reactant 1

HCID 2585Carvedilol

Product 2

HCID 2585CarvedilolHCID 17130052-(2-Methoxyphenoxy)ethyl amineYield 425.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Carvedilol (40 g) was dissolved in 150 ml of ethanol and 40 ml water. The solution was heated with agitation to 60-70° C. until the solid material was completely dissolved. The solution is then cooled with agitation to 10° C. over a period of 3 hours. After stirring the suspension for an additional 2.75 hours, the product is filtered. Pure Carvedilol Form III (35 g) was obtained.

Workup

  1. dissolutionwas completely dissolved
  2. temperatureThe solution is then cooled with agitation to 10° C. over a period of 3 hours
  3. filtrationthe product is filtered

Sources & evidence

ORD record
ord-431055c90377481491f6767ab526eefc
Source dataset
uspto-grants-2004_03
Patent number
US06699997B2

Reaction notes

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