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

HRID 1641115Notes

Reaction equation

HRID 1641115 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+]>O.CN1CCCC1=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 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-nitro-1-hydroxynaphthalene (10.0 g, 52.8 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (13.77 g, 74.0 mmol), NaOH (3.0 g, 74.0 mmol), K2CO3 (17.53 g, 126.8 mmol) and 1-methyl-2-pyrrolidinone (400 ml) is heated to 90-100° C. and held for 2-3 hours. The mixture is cooled to 40° C. and water (300 ml) is added. The mixture is cooled to 0° C. and held for 4 hours. The product is collected by filtration, washed with water, cyclohexane and dried under vacuum to constant weight to yield 4-[2-(4-nitro-naphthalen-1-yloxy)-ethyl]-morpholine 14.73 g, 92.6%.

Workup

  1. temperatureThe mixture is cooled to 40° C.
  2. temperatureThe mixture is cooled to 0° C.
  3. waitheld for 4 hours
  4. filtrationThe product is collected by filtration
  5. washwashed with water, cyclohexane
  6. customdried under vacuum to constant weight

Sources & evidence

ORD record
ord-0be0c428141e4915bc2f47369a5b326f
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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