Hydrochloric Acid → 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride

HRID 1188706Notes

Reaction equation

HRID 1188706 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[N:12]O)[CH2:9][CH2:8]2.[ClH:14]>C(O)(=O)C.CO.[Pd]>[ClH:14].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([NH2:12])[CH2:9][CH2:8]2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 5949007-Methoxyindan-1-one oxime

Product 1

HCID 667603987-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochlorideYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

7-methoxyindan-1-one oxime (2.92 g, 16 mmol) was dissolved in acetic acid (150 mL) and hydrogenated on the H-Cube: 1 mL/min flow rate, 80° C., 100 bar with 10% Pd/C. The reaction mixture was evaporated, the residue was dissolved in methanol and 1 equivalent of hydrochloric acid in methanol was added. The solvent was evaporated and the residue was triturated with diethyl ether to give 7-methoxy-1-aminoindane hydrochloride (2.38 g, 12 mmol, 75%). ESMS m/z 147 (M+H)+.

Workup

  1. custom1 mL/min flow rate, 80° C., 100 bar
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in methanol
  4. customThe solvent was evaporated
  5. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-5e3386a0225d4b36988ff9fc999d5365
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

Loading…