Reaction #432318

Reaction equation

hydrogen chloride

1-amino-2,3-dihydro-4,6-dimethyl-7-hydroxy-1H-indene

triethylamine

octyl chloride

→

2,3-dihydro-1-octylamino-4,6-dimethyl-7-hydroxy-1H-indene hydrochloride

Yield 15.1%

Solvents

chloroform

ethanol

ethanol

acetonitrile

Conditions

Workup

1. 1
   WashThe reaction mixture was washed with a diluted hydrochloric acid, water
2. 2
   Dryingan aqueous solution saturated with sodium bicarbonate, water and an aqueous soluction saturated with sodium chloride in this order, then dried with anhydrous sodium sulfate
3. 3
   OtherThe solvent was removed by evaporation
4. 4
   Otherthe residue thus obtained
5. 5
   workup.ADDITIONwas added
6. 6
   Otherthereto form a hydrochlodide

Procedure

To a solution containing 1.77 g of 1-amino-2,3-dihydro-4,6-dimethyl-7-hydroxy-1H-indene and 2 ml of triethylamine in 100 ml of chloroform was added dropwise 2.23 g of octyl chloride at room temperature. Then the reaction micture was stirred at the same temperature for 4 hours. The reaction mixture was washed with a diluted hydrochloric acid, water, an aqueous solution saturated with sodium bicarbonate, water and an aqueous soluction saturated with sodium chloride in this order, then dried with anhydrous sodium sulfate. The solvent was removed by evaporation and the residue thus obtained was dissolved in ethanol, tna an ethanol saturated with hydrogen chloride gas was added thereto form a hydrochlodide. Recrysttallized form acetonitrile to obtain 0.49 g of 2,3-dihydro-1-octylamino-4,6-dimethyl-7-hydroxy-1H-indene hydrochloride. Colorless needle-like crystals. Melting point: 120°-121° C.

Source