3-(4-Methoxyphenyl)propan-1-amine → 2-(Cyclohexylmethoxy)-1-ethanamine

HRID 1458425Notes

Reaction equation

HRID 1458425 reaction equation
CO[CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9]CCN)[CH2:5][CH2:4]1.C[O:14]C1C=CC(CCCN)=CC=1.C1(C[CH2:32][CH2:33][NH2:34])CCCCC1>O1CCOCC1>[CH:6]1([CH2:9][O:14][CH2:32][CH2:33][NH2:34])[CH2:5][CH2:4][CH2:3][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 30298153-(4-Methoxyphenyl)propan-1-amineHCID 126663903-CyclohexylpropylamineHCID 23302970200400-15-3

Product 1

HCID 233029322-(Cyclohexylmethoxy)-1-ethanamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[(cis) and (trans)]-3-(4-Methoxycyclohexyl)propylamine: A solution of 1.18 g (7.1 mmol) 3-(4-methoxyphenyl)propylamine in 50 mL of dioxane was hydrogenated at 138 bar and at 160° C. for 16 h in the presence of 0.5 g of 5% Ru/Al2O3. The catalyst was removed by filtration and the filtrate was concentrated to dryness. Preparative HPLC of the crude product by elution with 10% (10% concd NH4OH in MeOH)-CH2Cl2 furnished 723.5 mg (59%) of the cis/trans mixture of cyclohexylpropylamine (c/t=~3:1 by 1H NMR): 1H NMR (CDCl3, cis-isomer only) δ3.37 (br s, 1H), 3.27 (s, 3H), 2.64 (t, J=7.0 Hz, 2H), 2.10-0.87 (M, 15H); FDMS 172 (M+1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. washPreparative HPLC of the crude product by elution with 10% (10% concd NH4OH in MeOH)-CH2Cl2
  4. customfurnished

Sources & evidence

ORD record
ord-6093d3a2174043cb91020793cd2c9156
Source dataset
uspto-grants-1998_12
Patent number
US05849922

Reaction notes

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