Morpholine → 4-(4-Nitrobenzyl)morpholine

HRID 1179226Notes

Reaction equation

HRID 1179226 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C1COCC1>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7831834-(4-Nitrobenzyl)morpholineYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-bromomethyl-4-nitro-benzene (5.0 g, 29.1 mmol) and potassium carbonate (12.0 g, 87 mmol) in THF (100 mL) was added morpholine (6.35 mL, 73 mmol) in a slow stream. The reaction was stirred 24 h at room temperature, was filtered through Celite and evaporated. Purification by flash chromatography (SiO2) provided 4-(4-nitro-benzyl)-morpholine (5.27 g, 81% yield) as a pale yellow solid. 1H-NMR (DMSO-d6, 500 MHz) 8.20 (d, 2H), 7.60 (d, 2H), 3.61 (m, 6H), 2.38 (m, 4H) ppm; MS (FIA) 223.1 (M+H); HPLC (Method A) 1.577 min.

Workup

  1. filtrationwas filtered through Celite
  2. customevaporated
  3. customPurification by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-3caa4b24726a4b9f9998dc41fc0e2bfb
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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