Allyl bromide → rac. N-allyl-1-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine

HRID 1156544Notes

Reaction equation

HRID 1156544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][CH2:16][NH:17][CH3:18])[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CC(C)=O>[CH2:25]([N:17]([CH3:18])[CH2:16][CH2:15][C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]1)[CH:26]=[CH2:27]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 133240571-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine

Product 1

HCID 13324058rac. N-allyl-1-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.9 g of 1-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine are dissolved in 50 ml of acetone. Thereupon, 3.5 g of potassium carbonate are added, 1.8 ml of allyl bromide are slowly added dropwise while stirring, and the mixture is stirred overnight. Subsequently, the precipitate is removed by filtration, and the filtrate is evaporated, and rac. N-allyl-1-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine remains as the residue. The hydrochloride of this compound melts at 114°-116° C. (after recrystallization from ethyl acetate/diisopropyl ether).

Workup

  1. stirringthe mixture is stirred overnight
  2. customSubsequently, the precipitate is removed by filtration
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-1d5e6365ae9a488b9ecfafcb544012c5
Source dataset
uspto-grants-1982_06
Patent number
US04336268

Reaction notes

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