Sodium Hydroxide → 2-(2-Benzyloxy-4-isopropylphenyl)ethylamine

HRID 733348Notes

Reaction equation

HRID 733348 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[CH:24]=[CH:25][N+:26]([O-])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH2:7]([O:14][C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=1[CH2:24][CH2:25][NH2:26])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 688252572-Benzyloxy-4-isopropyl-1-(2-nitrovinyl)benzene

Product 1

HCID 178562302-(2-Benzyloxy-4-isopropylphenyl)ethylamineYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 3.01 g of lithium aluminum hydride in 100 mL of anhydrous diethyl ether was added dropwise a solution of 9.45 g of 2-benzyloxy-4-isopropyl-1-(2-nitro-vinyl)benzene in 10 mL of diethyl ether under ice-cooling with stirring during 10 minutes. After the mixture was stirred for 1 hour, 63.5 mL of 2 mol/L sodium hydroxide solution was added dropwise to the stirred reaction mixture under ice-cooling, and the mixture was stirred for 1 hour. To the mixture was added anhydrous sodium sulfate, and the mixture was stirred for 15 minutes. The insoluble material was filtered off through a diatomaceous earth, and 100 mL of water was added to the filtrate. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with saturated aqueous sodium bicarbonate solution, and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 8.56 g of 2-(2-benzyloxy-4-isopropylphenyl)-ethylamine.

Workup

  1. temperaturecooling
  2. stirringAfter the mixture was stirred for 1 hour
  3. temperaturecooling
  4. stirringthe mixture was stirred for 1 hour
  5. stirringthe mixture was stirred for 15 minutes
  6. filtrationThe insoluble material was filtered off through a diatomaceous earth, and 100 mL of water
  7. additionwas added to the filtrate
  8. extractionThe mixture was extracted with ethyl acetate
  9. washthe organic layer was washed successively with saturated aqueous sodium bicarbonate solution, and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6972b839d5ab496e87d14f7a803eefbc
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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