HCID 18007303, compound → HCID 18007284, compound

HRID 274044Notes

Reaction equation

HRID 274044 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20]C)=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Br>[CH2:1]([NH:8][CH:9]1[CH2:10][C:11]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:12]=2[CH2:13][CH2:14][CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 18007303HCID 18007303, compound

Product 1

HCID 18007284HCID 18007284, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (3.0 g) and 47% hydrobromic acid (106 ml) was stirred at 130° C. for 1.5 hours. After cooling, the reaction mixture was concentrated in vacuo. To the residue was added 28% ammonium hydroxide, and the whole was extracted once with ethyl acetate. The extract was washed twice with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; chloroform-methanol; 25:1 to 15:1) to give 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (1.9 g) as an oil, which solidified on standing.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionTo the residue was added 28% ammonium hydroxide
  4. extractionthe whole was extracted once with ethyl acetate
  5. washThe extract was washed twice with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (gradient elution; chloroform-methanol; 25:1 to 15:1)

Sources & evidence

ORD record
ord-20b978147d574123a3ff71ab03c3d2bd
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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