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

HRID 345136Notes

Reaction equation

HRID 345136 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[C:6]([CH3:13])[CH:7]=[C:8]([CH3:12])[C:9]=2[OH:11])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH2:21]([Cl:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>C(Cl)(Cl)Cl.C(O)C.C(#N)C>[ClH:29].[CH2:21]([NH:1][CH:2]1[C:10]2[C:5](=[C:6]([CH3:13])[CH:7]=[C:8]([CH3:12])[C:9]=2[OH:11])[CH2:4][CH2:3]1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 81421-ChlorooctaneHCID 8471TriethylamineHCID 12857262HCID 12857262, compound

Product 1

HCID 136559182,3-dihydro-1-octylamino-4,6-dimethyl-7-hydroxy-1H-indene hydrochlorideYield 15.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

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.

Workup

  1. washThe reaction mixture was washed with a diluted hydrochloric acid, water
  2. dry with materialan 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. customThe solvent was removed by evaporation
  4. customthe residue thus obtained
  5. additionwas added
  6. customthereto form a hydrochlodide

Sources & evidence

ORD record
ord-5c393ffbbf5f4ea1ae77778299073b47
Source dataset
uspto-grants-1991_10
Patent number
US05055474

Reaction notes

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