Dimethylamine → 2-(4-Aminophenyl)-N,N-dimethylacetamide

HRID 1937736Notes

Reaction equation

HRID 1937736 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.Cl.[CH3:13][N:14](C)[CH2:15]CCN=C=NCC.CNC.CCO>ClCCCl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:14]([CH3:15])[CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 145334-Aminophenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 128052272-(4-Aminophenyl)-N,N-dimethylacetamideYield 48.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 4-aminophenylacetic acid (5 g, 30 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (6.9 g, 36 mmol), and dimethylamine (6.5 mol of a 5.6M solution in EtOH 36 mmol) in 1,2, DCE was stirred at room temperature for 4 h. Silica was added, the suspension evaporated and residue loaded onto silica plug column, eluting with DCM:MeOH/98:2). The title compound (2.6 g, 45%) was isolated as an orange solid. 1H MNR (400 MHz, CDCl3) δ2.94 (3H, s), δ2.98 (3H, s), 3.60 (2H, s), 6.64 (2H, d, J=8.3 Hz), 7.03 (2H, d, 8.2 Hz). MS (CI)+179 (M+H)+.

Workup

  1. additionSilica was added
  2. customthe suspension evaporated
  3. washeluting with DCM

Sources & evidence

ORD record
ord-100b85f599074e5aa0e1fcaf7e4fa8b0
Source dataset
uspto-grants-2002_05
Patent number
US06395905B1

Reaction notes

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