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

HRID 2037009Notes

Reaction equation

HRID 2037009 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-444540948498480282d22c2eb1c34a68
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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