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4-Oxiranylmethoxy-9H-carbazole → 1-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}-3-(9H-carbazol-4-yloxy)propan-2-ol

HRID 1376199
Notes
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Reaction equation

HRID 1376199 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.[O:20]1[CH2:22][CH:21]1[CH2:23][O:24][C:25]1[C:37]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:1]([N: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])[CH2:22][CH:21]([OH:20])[CH2:23][O:24][C:25]1[C:37]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]=2[CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 50207104-Oxiranylmethoxy-9H-carbazoleHCID 11821241N-Benzyl-2-(2-methoxyphenoxy)ethylamine

Product 1

HCID 110383641-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}-3-(9H-carbazol-4-yloxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

35.0 g of benzyl-[2-(2-methoxy-phenoxy)-ethyl]-amine (136 mmol) were dissolved in 225 ml ethanol. To the stirred solution 30.1 g of 4-oxiranylmethoxy-9H-carbazole (126 mmol) were added and the mixture was heated under reflux for 15 h. The boiling solution was treated with 3 g of activated carbon for 30 min. The activated carbon was filtered off in the heat, and washed with 20 ml ethanol. The solution was stirred for 3 h at room temperature and next 5 h at 0° C. The product was filtered under suction and washed twice with 10 ml cold ethanol. The substance was dried at 50° C. for 12 h

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 h
  3. additionThe boiling solution was treated with 3 g of activated carbon for 30 min
  4. filtrationThe activated carbon was filtered off in the heat
  5. washwashed with 20 ml ethanol
  6. filtrationThe product was filtered under suction
  7. washwashed twice with 10 ml cold ethanol
  8. customThe substance was dried at 50° C. for 12 h

Sources & evidence

ORD record
ord-368af3ecde5b487abda167bf4f0e045d
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07169935B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes