3-Methoxyphenethylamine → HCID 60063665, compound

HRID 475931Notes

Reaction equation

HRID 475931 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](CCN)[CH:6]=[CH:7][CH:8]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH:21]([N:24](C(C)C)CC)(C)[CH3:22]>>[CH2:21]([N:24]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:22]

Participants

4

Reactant 3

HCID 748663-MethoxyphenethylamineHCID 76300Ethyl 4-bromobutyrateHCID 81531Diisopropylethylamine

Product 1

HCID 60063665HCID 60063665, compoundYield 95.2%

Procedure

(3-Methoxyphenyl)ethylamine 14 (5.73 gm, 0.038 moles), ethyl 4-bromobutyrate (9.60 gm, 0.049 moles) and diisopropylethylamine (6.40 gm, 0.050 moles) were heated at 110-120° C. overnight, cooled, and partitioned between 100 ml DCM and 100 ml water. The aqueous layer was extracted twice with 50 ml portions of DCM. The combined organic extracts were washed with saturated NaCl, dried over Na2SO4, filtered, and concentrated by rotary evaporation under reduced pressure. The crude product was purified by flash chromatography on silica gel, eluting with a gradient mixture of ethyl acetate and hexane. Ethyl 4-[ethyl(3-methoxyphenyl)amino]butanoate 15 (9.6 gm, 95% yield) was isolated as a slightly yellow oil after removing the solvent. 1H NMR (CDCl3) δ 7.12, 1H, t; 6.31, 1H, d; 6.22, 2H, m; 4.12, 2H, q; 3.79, 3H, s; 3.3, 4H, m; 2.35, 2H, t; 1.9, 2H, m; 1.26, 3H, t; 1.14, 3H, t.

Workup

  1. temperaturecooled
  2. custompartitioned between 100 ml DCM and 100 ml water
  3. extractionThe aqueous layer was extracted twice with 50 ml portions of DCM
  4. washThe combined organic extracts were washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica gel
  9. washeluting with a gradient mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f55f2316748e4b2ab365a6786fdc2c01
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Reaction notes

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