N-Ethylaniline → Ethyl 4-[ethyl(phenyl)amino]butanoate

HRID 475927Notes

Reaction equation

HRID 475927 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.Br[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(OCC)(=O)C>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 57145352Ethyl 4-[ethyl(phenyl)amino]butanoateYield 79.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-ethylaniline 5 (2.0 gm, 0.016 moles), triethylamine (5.0 ml, 0.036 moles), and ethyl 4-bromobutyrate (3.45 gm, 0.018 moles) were heated at 110° C. for 14 hours under argon. The mixture was cooled to room temperature, diluted with 50 ml ethyl acetate, washed with 50 ml water and 50 ml saturated NaCl, dried over MgSO4, filtered, and evaporated under reduced pressure to give crude ethyl 4-(ethylphenylamino)butanoate 6 (3.0 gm, 77% yield). 1H NMR (CDCl3) δ 7.2, 2H, m; 6.6; 3H, m; 4.15, 2H, q; 3.3, 4H, m; 2.38, 2H, t; 1.9, 2H, m; 1.25, 3H, t; 1.10, 3H, t.

Workup

  1. washwashed with 50 ml water and 50 ml saturated NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6d3761d0eebb4aceb83f373fc6a6b918
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Reaction notes

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