HCID 11234330, compound → 1-(9-Benzenesulfonyl-9H-carbazol-4-yloxy)-3-{benzyl-[2-(2-methoxy-phenoxy)-ethyl]-amino}-propan-2-ol

HRID 1376196Notes

Reaction equation

HRID 1376196 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([S:26]([N:29]2[C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([O:42][CH2:43][CH:44]4[CH2:46][O:45]4)[C:36]=3[C:35]3[C:30]2=[CH:31][CH:32]=[CH:33][CH:34]=3)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[C:20]1([S:26]([N:29]2[C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([O:42][CH2:43][CH:44]([OH:45])[CH2:46][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9][CH2:10][O:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[O:18][CH3:19])[C:36]=3[C:35]3[C:30]2=[CH:31][CH:32]=[CH:33][CH:34]=3)(=[O:27])=[O:28])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 11234330HCID 11234330, compoundHCID 11821241N-Benzyl-2-(2-methoxyphenoxy)ethylamine

Product 1

HCID 114792061-(9-Benzenesulfonyl-9H-carbazol-4-yloxy)-3-{benzyl-[2-(2-methoxy-phenoxy)-ethyl]-amino}-propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.4 g of benzyl-[2-(2-methoxy-phenoxy)-ethyl]-amine (29 mmol) were dissolved in 47 ml ethanol. To the stirred solution 10 g of 9-benzenesulfonyl-4-oxiranylmethoxy-9H-carbazole (26 mmol) were added and the mixture was heated under reflux for 15 h. The boiling solution was treated with 1 g of activated carbon for 30 min. The activated carbon was filtered off in the heat, and washed with 20 ml ethanol. The ethanol was rotary evaporated (Tbath 40° C., 20 mbar) and the crude material purified by liquid chromatography (eluent toluene/ethyl acetate 4:1), the pure fractions were collected and rotary evaporated (40° C./15 mbar).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 h
  3. additionThe boiling solution was treated with 1 g of activated carbon for 30 min
  4. filtrationThe activated carbon was filtered off in the heat
  5. washwashed with 20 ml ethanol
  6. customThe ethanol was rotary evaporated (Tbath 40° C., 20 mbar)
  7. customthe crude material purified by liquid chromatography (eluent toluene/ethyl acetate 4:1)
  8. customthe pure fractions were collected
  9. customrotary evaporated (40° C./15 mbar)

Sources & evidence

ORD record
ord-ea2ea3a62ccf4098ba3abd25ec982cd5
Source dataset
uspto-grants-2007_01
Patent number
US07169935B2

Reaction notes

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