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

HRID 544270Notes

Reaction equation

HRID 544270 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-21a3d3a1abb94371b81be2ae213de136
Source dataset
uspto-grants-1984_05
Patent number
US04448991

Reaction notes

Loading…