Methyl Bromide → 3-Benzylmethylamino-1-methylindan-1-ol

HRID 1287557Notes

Reaction equation

HRID 1287557 reaction equation
[CH3:1]Br.[Mg].[CH2:4]([CH2:11][NH:12][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH2:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O1CCCC1>[CH2:4]([CH2:11][NH:12][CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:1])([OH:22])[CH2:14]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6323Methyl Bromide2×HCID 5462224MagnesiumHCID 215052573-Benzylmethylaminoindan-1-one

Product 1

HCID 215052773-Benzylmethylamino-1-methylindan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 35 milliliters of tetrahydrofuran, 4 grams methyl bromide is dissolved. One quarter of this solution is then added to 1 gram of magnesium, previously washed with chloroform, and refluxed with tetrahydrofuran for 20 minutes; and this mixture is refluxed 4 hours to initiate reaction. Additional methyl bromide solution is thereafter added to maintain the refluxing without further heating. After the addition has been completed 10 grams of 3-benzylmethylaminoindan-1-one is added and the mixture is refluxed for 2 hours. The reactants are allowed to stand overnight and then poured onto ice-cold ammonium chloride solution. Tetrahydrofuran is added and the two layers formed are allowed to separate. The solvent layer is decanted off and the aqueous layer is extracted twice with 10 milliliters of tetrahydrofuran which are decanted off and combined with the remaining solvent layer. The organic phase is dried over anhydrous magnesium sulphate, filtered and evaporated to dryness to yield 3-benzylmethylamino-1-methylindan-1-ol as a yellow oil.

Workup

  1. washpreviously washed with chloroform
  2. temperaturerefluxed with tetrahydrofuran for 20 minutes
  3. temperatureand this mixture is refluxed 4 hours
  4. customreaction
  5. temperatureto maintain the refluxing without further heating
  6. additionAfter the addition
  7. additionis added
  8. temperaturethe mixture is refluxed for 2 hours
  9. additionpoured onto ice-cold ammonium chloride solution
  10. customthe two layers formed
  11. customto separate
  12. customThe solvent layer is decanted off
  13. extractionthe aqueous layer is extracted twice with 10 milliliters of tetrahydrofuran which
  14. customare decanted off
  15. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  16. filtrationfiltered
  17. customevaporated to dryness

Sources & evidence

ORD record
ord-44e2533b96ce4265abfc1f621bdb2b36
Source dataset
uspto-grants-1976_10
Patent number
US03985729

Reaction notes

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