Water → N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide Hydrochloride

HRID 1039283Notes

Reaction equation

HRID 1039283 reaction equation
[NH2:1][C:2]1[C:10]([O:11]C)=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:4][CH:3]=1.B(Br)(Br)Br.O.[Cl:24]CCl>C(OCC)(=O)C>[ClH:24].[NH2:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6344Dichloromethane3×HCID 25134Boron tribromide2×HCID 57781264N-[2-(6-amino-7-methoxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide

Product 1

HCID 67354374N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide HydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N-[2-(6-amino-7-methoxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide (2.56 g, 10.3 mmol) in dichloromethane (80 mL) was added a solution of boron tribromide in dichloromethane (1M, 22.7 mL, 22.7 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1.5 hr. To the reaction solution was added water, and the mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane (80 mL), a solution of boron tribromide in dichloromethane (1M, 22.7 mL, 22.7 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 1.5 hr. To the reaction solution was added water, and the mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and converted to hydrochloride with 4N hydrochloric acid/ethyl acetate solution. The solvent was evaporated under reduced pressure to give the title compound (2.51 g, yield 90%).

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane (80 mL)
  6. temperaturecooling
  7. stirringthe mixture was stirred at room temperature for 1.5 hr
  8. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4cfa7a43364944fd9e5421a90d1dab56
Source dataset
uspto-grants-2013_10
Patent number
US08552037B2

Reaction notes

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