Aluminium lithium hydride → 3-Methoxy-4-phenylmethoxyphenylisopropylamine

HRID 1607732Notes

Reaction equation

HRID 1607732 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16]([N+:18]([O-])=O)[CH3:17])=[CH:11][C:10]=1[O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH2:18])[CH3:17])=[CH:11][C:10]=1[O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 534221341-Benzyloxy-2-methoxy-4-(2-nitropropenyl)benzene

Product 1

HCID 145794523-Methoxy-4-phenylmethoxyphenylisopropylamineYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 6.78 g of 1-(4-benzyloxy-3-methoxy-phenyl)-2-nitropropene is added dropwise to a suspension of 2.15 g of lithium aluminum hydride in tetrahydrofuran. The mixture is stirred at room temperature and then refluxed. After the reaction, excess lithium aluminum hydride is decomposed with ice water, and inorganic materials are filtered off. The filtrate is washed, dried and then condensed to dryness. 6 g of 1-(4-benzyloxy-3-methoxyphenyl)-2-aminopropane are obtained as pale yellow viscous oil.

Workup

  1. temperaturerefluxed
  2. filtrationare filtered off
  3. washThe filtrate is washed
  4. customdried
  5. customcondensed to dryness

Sources & evidence

ORD record
ord-b8afb5521a7b43cba946b0a0176db700
Source dataset
uspto-grants-1989_09
Patent number
US04866196

Reaction notes

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