Water → HCID 135752, compound

HRID 544273Notes

Reaction equation

HRID 544273 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=O)[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][CH2:16][N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20459997HCID 20459997, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 135752HCID 135752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.0 g of 1-(m-methoxyphenyl)-N,N-dimethyl-3-cyclohexene-1-acetamide in 10 ml of absolute tetrahydrofuran is added to a suspension of 1 g of lithium aluminum hydride in 50 ml of absolute tetrahydrofuran, and the mixture is boiled at reflux overnight. After the addition of water, the separated precipitate is removed by filtration under suction and washed well with tetrahydrofuran, whereupon the filtrate is evaporated. The oil remaining behind is treated with 1 N hydrochloric acid. The neutral portion is taken up in ether. The acidic phase is made alkaline by the addition of concentrated ammonia and the liberated rac. 1-(m-methoxyphenyl)-N,N-dimethyl-2-cyclohexene-1-ethylamine is taken up in methylene chloride. The hydrochloride of this compound melts at 161°-162° C. (after recrystallization from ethyl acetate/ethanol).

Workup

  1. temperatureat reflux overnight
  2. customthe separated precipitate is removed by filtration under suction
  3. washwashed well with tetrahydrofuran, whereupon the filtrate
  4. customis evaporated
  5. additionThe oil remaining behind is treated with 1 N hydrochloric acid
  6. additionby the addition of concentrated ammonia

Sources & evidence

ORD record
ord-722d07ab9c024a47b67a60a0a95e3fb9
Source dataset
uspto-grants-1984_05
Patent number
US04448991

Reaction notes

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