1,5-Dimethyl 2-methylenepentanedioate → 1-(2,4-Dimethoxybenzyl)-6-oxopiperidine-3-carboxylic Acid Methyl Ester

HRID 83508Notes

Reaction equation

HRID 83508 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4](=[CH2:11])[CH2:5][CH2:6][C:7](OC)=[O:8].[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][CH2:6][C:7](=[O:8])[N:18]([CH2:17][C:16]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=2[O:14][CH3:13])[CH2:11]1)=[O:12]

Participants

4

Reactant 2

HCID 5745371,5-Dimethyl 2-methylenepentanedioateHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 712878151-(2,4-Dimethoxybenzyl)-6-oxopiperidine-3-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-methylenepentanedioic acid dimethyl ester (19.2 g) in toluene (195 ml) was added 2,4-dimethoxybenzylamine (16.6 ml), and the mixture was stirred for 3 days at reflux. This reaction solution was cooled to room temperature, and then washed with a 1M aqueous solution of hydrochloric acid, water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product of the titled compound (26.8 g).

Workup

  1. temperatureat reflux
  2. washwashed with a 1M aqueous solution of hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4b6b70399b9472ebdbce97fd404ebe8
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

Loading…