Potassium Carbonate → 4-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholine

HRID 243814Notes

Reaction equation

HRID 243814 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 3438294-Nitro-1-naphthol

Product 1

HCID 119912044-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholineYield 88.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-nitronaphthalen-1-ol (10.1 g, 53.4 mmol), 4-(2-chloroethyl)morpholine.hydrochloride (14.0 g, 75.2 mmol), sodium hydroxide (3.11 g, 77.8 mmol) and potassium carbonate (17.5 g, 127 mmol) in 1-methylpyrrolidine-2-one (180 mL) was stirred at 100° C. After 3 hours, the reaction solution was cooled to 0° C., water (200 mL) was added thereto, followed by stirring the mixture. The precipitated crystals were collected by filtration to obtain 14.31 g of the captioned compound (88% yield).

Workup

  1. temperaturethe reaction solution was cooled to 0° C.
  2. stirringby stirring the mixture
  3. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-adce5766880b421e8cfc0f5bbebd1de0
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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