Methylamine → 1-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine

HRID 544279Notes

Reaction equation

HRID 544279 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][CH:16]=O)[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:18][NH2:19]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([CH2:15][CH2:16][NH:19][CH3:18])[CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 204600121-(m-Methoxyphenyl)-2-cyclohexene-1-acetaldehyde

Product 1

HCID 133240571-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of 1-(m-methoxyphenyl)-2-cyclohexene-1-acetaldehyde is dissolved in 10 ml of methanol, and after treatment with 10 ml of methylamine, the mixture is stirred at room temperature overnight with a magnetic stirrer in a bomb tube. After evaporation of the solvent, the residue is dissolved in ethanol. Then, the solution is treated with 0.5 g of sodium borohydride, stirred at room temperature for 2 hours. The solvent is removed by evaporation, and the residue is taken up with 3 N hydrochloric acid. The aqueous phase is extracted with ether and made alkaline by the addition of concentrated ammonia, whereupon the resulting rac. 1-(m-methoxyphenyl)-N-methyl-2-cyclohexene-1-ethylamine is taken up in methylene chloride. The hydrochloride of this compound melts at 177°-179° C.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in ethanol
  3. additionThen, the solution is treated with 0.5 g of sodium borohydride
  4. customThe solvent is removed by evaporation
  5. extractionThe aqueous phase is extracted with ether
  6. additionby the addition of concentrated ammonia

Sources & evidence

ORD record
ord-5bd01f41ca7742e5b3f04829dd79e5d7
Source dataset
uspto-grants-1984_05
Patent number
US04448991

Reaction notes

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