Morpholine → 4-(4-Nitrobenzyl)morpholine

HRID 2174217Notes

Reaction equation

HRID 2174217 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(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>ClCCl>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7831834-(4-Nitrobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1-(bromomethyl)-4-nitro-benzene (250 mg, 1.157 mmol) in dichloromethane (5 mL) was treated with triethylamine (200 μL, 1.39 mmol) and morpholine (110 μL, 1.27 mmol) then stirred at room temperature for 1.5 hrs. The solution was diluted with dichloromethane (20 mL) then washed with water (2×20 mL). The organic extract was dried (MgSO4), filtered and concentrated to give (i) which was used in subsequent reactions without further purification. 1H NMR (400 MHz, CDCl3) δ 8.21-8.16 (m, 2H), 7.56-7.50 (m, 2H), 3.76-3.69 (m, 4H), 3.59 (s, 2H), 2.49-2.42 (m, 4H).

Workup

  1. washthen washed with water (2×20 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-59f060960c034484a13891d0904b51f2
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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