Diisopropylamine → N-(2-Morpholinoethyl)-4-nitroaniline

HRID 11511

Reaction equation

HRID 11511 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[N:11]1([CH2:17][CH2:18][NH2:19])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(NC(C)C)(C)C>O1CCOCC1.ClCCl>[N:11]1([CH2:17][CH2:18][NH:19][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 9590p-FluoronitrobenzeneHCID 4082852-Morpholinoethylamine

Product 1

HCID 21975017N-(2-Morpholinoethyl)-4-nitroaniline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 7.5 mL of p-fluoronitrobenzene, 10.25 mL 2-morpholin-4-yl-ethylamine and 15 mL N,N-diisopropylamine in 36 mL dioxane is heated at 105° C. for 2 days. The reaction mixture is cooled to room temperature, diluted with dichloromethane (360 mL) and washed with water (3×290 mL). Upon evaporation to dryness, the dichloromethane layer yields the (2-morpholin-4-yl-ethyl)-(4-nitro-phenyl)-amine product, which is recrystallized from methanol.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water (3×290 mL)
  3. customUpon evaporation to dryness

Sources & evidence

ORD record
ord-e48903f80f9f421c91edcec7605af2eb
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Linked notes

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