N-Methylaniline → Ethyl 5-[methyl(phenyl)amino]pentanoate

HRID 2225895Notes

Reaction equation

HRID 2225895 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)(O)[O-].[Na+]>>[CH3:1][N:2]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 7515N-MethylanilineHCID 84580Ethyl 5-bromovalerateHCID 516892Sodium Bicarbonate

Product 1

HCID 19438629Ethyl 5-[methyl(phenyl)amino]pentanoateYield 84.1%

Conditions

Temperature
110 °C

Procedure

A mixture of N-methylaniline (16 g) and ethyl 5-bromovalerate (30.2 g) was stirred at 110° C. for 22 hours. Then the mixture was made alkaline with an aqueous sodium bicarbonate. The resulting mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. The residue was distilled under reduced pressure to obtain ethyl 5-(N-methylanilino)valerate (28.6 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-b4bbe2adf4c64a9e8b088fcf64822498
Source dataset
uspto-grants-1994_09
Patent number
US05344928

Reaction notes

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