Triethylamine → 3-Methoxy-N-(1-methylazetidin-3-yl)-4-nitrobenzamide

HRID 1487648Notes

Reaction equation

HRID 1487648 reaction equation
[CH3:1][N:2]1[CH2:5][CH:4]([NH2:6])[CH2:3]1.C(N(CC)CC)C.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[C:19](Cl)=[O:20]>C(Cl)Cl>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[C:19]([NH:6][CH:4]1[CH2:5][N:2]([CH3:1])[CH2:3]1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111276553-methoxy-4-nitro-benzoyl ChlorideHCID 187126621-Methylazetidin-3-amine

Product 1

HCID 867264813-Methoxy-N-(1-methylazetidin-3-yl)-4-nitrobenzamideYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methylazetidin-3-amine (1 equiv) in dry DCM (0.13 M) was added triethylamine (1.8 equiv). A solution of 3-methoxy-4-nitrobenzoyl chloride (0.91 equiv) in dry DCM was added and the reaction was stirred at room temperature for 5 min. The mixture was then concentrated and purified by silica gel chromatography (5% MeOH in DCM) to afford the title compound (46.4% yield) as a yellow solid. MS (ESI) m/z 266.1 [M+H]+.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by silica gel chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-4052af470ca04efbbef86e4bea4225e2
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

Loading…