Diethyl Ether → N-Methylhomoveratrylamine

HRID 2396802Notes

Reaction equation

HRID 2396802 reaction equation
CO[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=O.C(OCC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(Cl)Cl>O1CCCC1>[CH3:3][NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 4128531HCID 4128531, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 77039N-Methylhomoveratrylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of (i) was reduced in dry tetrahydrofuran or diethylether in conventional manner by the addition of 3 equivalents of LiAlH4 and subsequent refluxing of the mixture for 0.5-1 hr. After cooling and filtration, the solvent was evaporated and the product obtained by first extraction of the ethereal phase at pH 4, then at pH 10 with methylene chloride. Drying and evaporation of the solvent yielded 50-60% nearly pure oily product.

Workup

  1. temperaturesubsequent refluxing of the mixture for 0.5-1 hr
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. customthe solvent was evaporated
  5. customthe product obtained by first extraction of the ethereal phase at pH 4
  6. customDrying
  7. customevaporation of the solvent
  8. customyielded 50-60% nearly pure oily product

Sources & evidence

ORD record
ord-bd266cbdf6bb41e0b400ff2f40e7548b
Source dataset
uspto-grants-1996_02
Patent number
US05494933

Reaction notes

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