Water → 4-[2-(4-Nitrophenyl)ethyl]morpholine

HRID 254943Notes

Reaction equation

HRID 254943 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.C([O-])([O-])=O.[K+].[K+].O>CC(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 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromide

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-(2-bromoethyl)-4-nitrobenzene (460 mg, 2.0 mmol) in acetone (15 mL) was added morpholine (610 mg, 7.0 mmol) and 680 mg of K2CO3. The mixture was stirred for 80 hours at ambient temperature, and then poured into water. The aqueous mixture was extracted with ether. The organic layer was washed with brine, dried over MgSO4, and evaporated in vacuo to give 456 mg (1.93 mmol; 97%) of the title compound, which was converted to the appropriate amine by the method disclosed in Preparation 16.

Workup

  1. extractionThe aqueous mixture was extracted with ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d56e25df96604da88774580088e98d59
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

Loading…