Morpholine → 4-(1-(4-Nitrophenyl)ethyl)morpholine

HRID 1179228Notes

Reaction equation

HRID 1179228 reaction equation
Br[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C=O)C>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH3:3])=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 110206791-(1-Bromoethyl)-4-nitrobenzene

Product 1

HCID 133988034-(1-(4-Nitrophenyl)ethyl)morpholineYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(1-bromo-ethyl)-4-nitro-benzene (1.24 g, 5.43 mmol), potassium carbonate (2.25 g, 16.3 mmol) and morpholine (1.2 mL, 13.6 mmol) in DMF (10 mL) was stirred at room temperature for 16 h, then evaporated. The residue was suspended in ethyl acetate, washed with water and brine, dried (sodium sulfate) and evaporated to provide 4-[1-(4-nitro-phenyl)-ethyl]-morpholine (1.225 g, 95% yield) as a yellow oil. 1H-NMR (DMSO-d6, 500 MHz) 8.19 (d, 2H), 7.16 (d, 2H), 3.56 (m, 5H), 2.41 (m, 2H), 2.26 (m, 2H), 1.29 (d, 3H) ppm; MS (FIA) 237.2 (M+H); HPLC (Method A) 2.248 min.

Workup

  1. customevaporated
  2. washwashed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-c94c1f28205849a09d15413d011c366a
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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