Hydrochloric Acid → 7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-amine

HRID 1425566Notes

Reaction equation

HRID 1425566 reaction equation
[F:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:23]=[C:22]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([NH:24]C(=O)OC(C)(C)C)=[CH:19][C:20]=3[NH:21]2)=[CH:13][CH:12]=1.Cl>O1CCOCC1>[F:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:23]=[C:22]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([NH2:24])=[CH:19][C:20]=3[NH:21]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58160266tert-butyl 7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-ylcarbamate

Product 1

HCID 582252137-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-amineYield 95.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-ylcarbamate (130 mg, 0.3 mmol) was added 10 mL of a 4 M HCl in dioxane solution. The mixture was stirred at rt for 5 h and concentrated under reduced pressure. The residue was washed with ether (15 mL) and suspended in EtOAc (50 mL). To this suspension was added 10 mL of a NaHCO3 (sat.) and the mixture was stirred for 5 min. The organic layer was dried over MgSO4 and concentrated to afford 7-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-9H-carbazol-2-amine as a brown solid (95 mg, 95%). MS (ESI) m/z 333 (M+H+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe residue was washed with ether (15 mL)
  3. additionTo this suspension was added 10 mL of a NaHCO3 (sat.)
  4. stirringthe mixture was stirred for 5 min
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ffc60e510c124d31996eb6696dd48166
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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