Benzoic Acid → HCID 86602151, compound

HRID 254872Notes

Reaction equation

HRID 254872 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH3:19][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[O:23][CH2:24][CH2:25][NH2:26].[C:31]([OH:39])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(O)C>[CH3:19][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[O:23][CH2:24][CH2:25][NH:26][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]=12.[C:31]([O-:39])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 50207104-Oxiranylmethoxy-9H-carbazole

Product 1

HCID 86602151HCID 86602151, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A mixture of 4-(oxiran-2-ylmethoxy)-9H-carbazole (II) (25.0 g, 104.60 mmole) and 62.5 ml 2-propanol is heated to 70° C. to 80° C. To this 2-(2-methoxyphenoxy)ethylamine (III) (25.33 g, 151.67 mmole) is added in one lot. The temperature of reaction mass is raised to reflux (80° C. to 85° C.) and maintained at this temperature for 1 hour. After that, this reaction mass was added to the pre-heated (80° C. to 85° C.) solution of benzoic acid (18.5 g) in 2-propanol (287.5 ml) and continued the reflux for next 2-hour, cooled to 50° C. to 55° C. and maintained the same temperature for 1 hr. The product filtered at same temperature followed by three 33.5 ml wash with hot (50° C. to 55° C.) 2-propanol. The wet product dried at 60° C. to 65° C. for 6-8 hours or till constant weight gives 36.5 g of Carvedilol benzoate (Yield=66%).

Workup

  1. temperatureis heated to 70° C. to 80° C
  2. customThe temperature of reaction mass
  3. temperatureis raised
  4. temperatureto reflux (80° C. to 85° C.)
  5. temperaturemaintained at this temperature for 1 hour
  6. additionAfter that, this reaction mass was added to the
  7. temperaturereflux for next 2-hour
  8. temperaturecooled to 50° C. to 55° C.
  9. temperaturemaintained the same temperature for 1 hr
  10. filtrationThe product filtered at same temperature
  11. washwash with hot (50° C. to 55° C.) 2-propanol
  12. customThe wet product dried at 60° C. to 65° C. for 6-8 hours or till constant weight

Sources & evidence

ORD record
ord-be49ebac7dff43fd9f4fd7cbe8b7a8b1
Source dataset
uspto-grants-2011_01
Patent number
US07875730B2

Reaction notes

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