Aluminium lithium hydride → alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

HRID 2287132Notes

Reaction equation

HRID 2287132 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH:13]([CH3:27])[CH2:14][C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH2:18][CH:17]=[CH:16]1)[C:10](=O)[CH3:11])[CH3:8]>O1CCCC1>[CH3:27][CH:13]([N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])[CH2:14][C:15]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:16]=[CH:17][CH2:18][CH:19]=[CH:20]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23459464N-ethyl-N-[1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethyl]-acetamide

Product 1

HCID 23459444alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.266 g. of lithium aluminum hydride is placed in 10 ml. of tetrahydrofuran. After the addition of 1 g. of N-ethyl-N-[1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)ethyl]-acetamide in 10 ml. of tetrahydrofuan, the mixture is stirred at room temperature for 7 hours. Subsequently, excess lithium aluminum hydride is destroyed by the addition of ethyl aceate and of water. The mixture is filtered and the filter is rinsed with ether. After separation of the phases, the organic phase is dried with sodium sulfate, filtered and concentrated completely. The crude product is chromatographed on 60 g. of Alox neutral with ethyl acetate. There is obtained α-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine in the form of an oily product. This is converted as usual into the hydrochloride which, after crystallization from methylene chloride/ether, has a melting point of 172°-174° C.

Workup

  1. additionAfter the addition of 1 g
  2. customSubsequently, excess lithium aluminum hydride is destroyed by the addition of ethyl aceate and of water
  3. filtrationThe mixture is filtered
  4. washthe filter is rinsed with ether
  5. customAfter separation of the phases
  6. dry with materialthe organic phase is dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated completely
  9. customThe crude product is chromatographed on 60 g

Sources & evidence

ORD record
ord-2ce233b2a07643afae2f65b8c531c8d2
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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