Sodium Hydroxide → 3-Methoxy-4-phenylmethoxyphenylisopropylamine

HRID 1884262Notes

Reaction equation

HRID 1884262 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[C:22]([N+:24]([O-])=O)[CH3:23])=[CH:17][C:16]=1[O:27][CH3:28])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH2:24])[CH3:23])=[CH:17][C:16]=1[O:27][CH3:28])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 534221341-Benzyloxy-2-methoxy-4-(2-nitropropenyl)benzene

Product 1

HCID 145794523-Methoxy-4-phenylmethoxyphenylisopropylamineYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.03 g (27.1 mmol) of lithium aluminum hydride and 20 ml of anhydrous tetrahydrofuran, an anhydrous tetrahydrofuran solution of 2.70 g (9.03 mmol) of 1-benzyloxy-2-methoxy-4-(2-nitropropenyl)benzene was added dropwise under vigorous stirring over about 90 minutes and refluxed for 2 hours by heating. The reaction mixture was cooled and aqueous sodium hydroxide solution was added thereto. After the precipitates were filtered off with celite-precoated glass filter, the solvent was distilled off from the filtrate under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated brine, dried over potassium carbonate and the solvent was distilled off under reduced pressure to give 2.30 g of crude 2-(4-benzyloxy-3-methoxyphenyl)-1-methylethylamine.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureby heating
  3. temperatureThe reaction mixture was cooled
  4. filtrationAfter the precipitates were filtered off with celite-precoated glass
  5. filtrationfilter
  6. distillationthe solvent was distilled off from the filtrate under reduced pressure
  7. extractionThe residue was extracted with ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialdried over potassium carbonate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-06d620cfac2d4d7795258987f215d516
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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