Water → 4-(2-(2-Chloro-3-nitrophenoxy)ethyl)morpholine

HRID 624791Notes

Reaction equation

HRID 624791 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.O>CN(C=O)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 3013917Phenol, 2-chloro-3-nitro-

Product 1

HCID 583144114-(2-(2-Chloro-3-nitrophenoxy)ethyl)morpholineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-chloro-3-nitrophenol (1 g, 5.8 mmol) was dissolved in DMF (6 mL). K2CO3 (1.6 g, 11.5 mmol) was added and the solution changed from yellow to red. 4-(2-chloroethyl)morpholine hydrochloride (1.07 g, 5.8 mmol) was added and the solution was allowed to stir for 15 h. The reaction was poured into H2O (30 mL) and extracted with EtOAc (3×30 mL). The organics were washed with 1N NaOH (100 mL) and brine (100 mL) and then dried over MgSO4, filtered, and concentrated in vacuo to provide 4-(2-(2-chloro-3-nitrophenoxy)ethyl)morpholine (1.4 g, 87%) as a golden oil.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe organics were washed with 1N NaOH (100 mL) and brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e96e27b9ff24d6fa15bbbf21fa1d4aa
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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