p-Fluoronitrobenzene → N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

HRID 723343Notes

Reaction equation

HRID 723343 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][OH:16].[OH-].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][O:16][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 766463-(Dimethylamino)-1-propanol

Product 1

HCID 10353575N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

Reagents, catalysts & solvents 1

HCID 21218Trioctylmethylammonium chlorideCatalyst

Conditions

Temperature
85 °C

Procedure

A mixture of 4-fluoronitrobenzene (2.82 g), 3-dimethylaminopropanol (2.48 g), powdered potassium hydroxide (1.35 g) and Aliquat® 336 (tricaprylylmethylammonium chloride) was heated at 85° C. for one hour. The cooled crude mixture was purified by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1 mixed with 1% v/v triethylamine). The product with the molecular weight of 224.26 (C11H16N2O3); MS (ESI): 225 ([M+H]+), was obtained in this way.

Workup

  1. temperatureThe cooled crude mixture
  2. customwas purified by chromatography on silica gel (eluent
  3. additionethyl acetate/methanol 9:1 mixed with 1% v/v triethylamine)
  4. customMS (ESI): 225 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-dd8a71a51534441a838d5c10f8a14915
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

Loading…