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

HRID 1733859Notes

Reaction equation

HRID 1733859 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-58856c818b6a455fb81177fa567be544
Source dataset
uspto-grants-1996_07
Patent number
US05532171

Reaction notes

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