Benzene → 3-Benzylamino-1-indanol

HRID 65837

Reaction equation

HRID 65837 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[CH2:2]1.C1C=CC=CC=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>CO.O>[CH2:18]([NH:25][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]([OH:11])[CH2:2]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 7504BenzylamineHCID 118151,3-IndandioneHCID 4311764Sodium borohydride

Product 1

HCID 227560943-Benzylamino-1-indanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Stir indan-1,3-dione (7.31 g.), benzene (200 ml.) and benzylamine (5.90 g.) and reflux into a water separator for 6 hours. Cool, filter, and wash the dark solid with ether. Boil the solid with methylene chloride, filter and remove the solvent by boiling and replace with ether. Filter to get 4.51 g. of dark solid. Stir 4.30 g. of this solid with methanol (150 ml.) and add sodium borohydride (12.0 g.) portionwise with stirring over 4 hours. Let the reaction stand at room temperature then evaporate the solvent in vacuo and digest the residue with water and ether. Extract the mixture with ether and wash, dry and evaporate the solvent in vacuo. Recrystallize the residue from cyclohexane-ether to obtain 1.996 g. of the pure free base of the title compound, m.p. 121°-125°.

Workup

  1. temperatureCool
  2. filtrationfilter
  3. washwash the dark solid with ether
  4. filtrationBoil the solid with methylene chloride, filter
  5. customremove the solvent
  6. filtrationFilter
  7. customto get 4.51 g
  8. stirringwith stirring over 4 hours
  9. customat room temperature
  10. customthen evaporate the solvent in vacuo
  11. extractionExtract the mixture with ether
  12. washwash
  13. customdry
  14. customevaporate the solvent in vacuo
  15. customRecrystallize the residue from cyclohexane-ether
  16. customto obtain 1.996 g

Sources & evidence

ORD record
ord-d5d463a177f34d02b1412d12bf02bce3
Source dataset
uspto-grants-1978_12
Patent number
US04129561

Linked notes

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