Methanol → 3-(Allyloxy)-1-(3-methoxyphenyl)propan-1-amine

HRID 501684Notes

Reaction equation

HRID 501684 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH:7]([NH:16]C(=O)C(F)(F)F)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH2:1]([O:4][CH2:5][CH2:6][CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[NH2:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86622320N-(3-(allyloxy)-1-(3-methoxyphenyl)propyl)-2,2,2-trifluoroacetamide

Product 1

HCID 684659353-(Allyloxy)-1-(3-methoxyphenyl)propan-1-amineYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step R (3): N-(3-(Allyloxy)-1-(3-methoxyphenyl)propyl)-2,2,2-trifluoroacetamide from step R (2) (610 mg, 1.92 mmol), potassium carbonate (1.33 g, 9.26 mmol), methanol (50 mL) and H2O (4 mL) were heated to reflux for 16 h. The mixture was concentrated in vacuo. H2O was added, and the aqueous layer was extracted several times with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford 390 mg (92% yield) of 3-(allyloxy)-1-(3-methoxyphenyl)propan-1-amine as a pale-yellow oil. The crude mixture was used without further purification. LC-MS (M+H)+=222.95; 1H NMR (300 MHz, CDCl3) δ ppm 1.82-2.18 (m, 2H) 3.23-3.54 (m, 3H) 3.72-3.82 (m, 3H) 3.83-4.00 (m, 2H) 4.14 (t, J=6.95 Hz, 1H) 5.08-5.31 (m, 2H) 5.76-5.95 (m, 1H) 6.71-6.86 (m, 1H) 6.86-6.97 (m, 1H) 7.14-7.29 (m, 2H).

Workup

  1. temperatureto reflux for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additionH2O was added
  4. extractionthe aqueous layer was extracted several times with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6bb2d28c33244a168a95d9051a03102c
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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