Sodium Iodide → 4-[2-(4-Nitrophenyl)ethyl]morpholine

HRID 1190155Notes

Reaction equation

HRID 1190155 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[I-].[Na+]>CN(C)C(=O)C.CCOC(C)=O>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 792664-Nitrophenethyl bromide

Product 1

HCID 27974734-[2-(4-Nitrophenyl)ethyl]morpholine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2-bromo-ethyl)-4-nitro-benzene (0.740 g, 3.22 mmol), morpholine (0.840 mL, 9.65 mmol), and sodium iodide (0.480 g, 3.22 mmol) in N,N-dimethylacetamide (3 mL) was heated at 80° C. for 10 min. The mixture was diluted with 30 mL EtOAc and washed with H2O (2×30 mL) and brine (30 mL) and dried over Na2SO4 to give the title compound as a yellow oil of sufficient purity to use in the next step. Mass spectrum (ESI, m/z): Calcd. for C12H16N2O3, 237.1 (M+H). found 237.2.

Workup

  1. washwashed with H2O (2×30 mL) and brine (30 mL)
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-bf019c58fa0842c094a6405379b50119
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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