1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(2,4-dimethoxybenzyl)piperidin-2-one

HRID 83510Notes

Reaction equation

HRID 83510 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH:8]([C:13]([OH:15])=O)[CH2:7]1.[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[NH:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[N:30]1[C:13]([CH:8]1[CH2:7][N:6]([CH2:5][C:4]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:3]=2[O:2][CH3:1])[C:11](=[O:12])[CH2:10][CH2:9]1)=[O:15])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 63362718HCID 63362718, compound

Product 1

HCID 712878795-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(2,4-dimethoxybenzyl)piperidin-2-oneYield 64.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(2,4-dimethoxybenzyl)-6-oxopiperidine-3-carboxylic acid (3.39 g) in chloroform (15 ml) were sequentially added (R)-4-benzyl-2-oxazolidinone (2.04 g), WSC.HCl (2.44 g) and 4-dimethylaminopyridine (706 mg) at room temperature, and the mixture was stirred overnight. This reaction mixture was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=4/1 to 1/1) to give the titled compound (low-polarity component 3.37 g, high-polarity component 2.72 g).

Workup

  1. customat room temperature
  2. customThis reaction mixture was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=4/1 to 1/1)

Sources & evidence

ORD record
ord-38c18ab6340345a9bd74f345470745d1
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

Loading…