Morpholine → HCID 66632716, compound

HRID 659157Notes

Reaction equation

HRID 659157 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[F:12].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[F:12][C:4]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 591391511-(Bromomethyl)-2-fluoro-3-nitrobenzene

Product 1

HCID 66632716HCID 66632716, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 1-(bromomethyl)-2-fluoro-3-nitrobenzene (2.50 g, 10.6 mmol) and morpholine (2.78 g, 32.0 mmol) in toluene (24 mL) was heated at reflux temperature for 2.5 h. The reaction mixture was allowed to cool to room temperature and then washed with 1 N NaOH (2×20 mL). The aqueous layer was extracted with EtOAc (2×25 mL), and the combined toluene solution and EtOAc extracts were dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 4-(2-fluoro-3-nitrobenzyl)morpholine (1.95 g, 89%) as a light yellow solid. 1H NMR (400 MHz, CD3OD): δ 8.02-7.97 (m, 1H), 7.83-7.78 (m, 1H), 7.36 (td, 1H, J=8.0, 1.0 Hz), 3.70-3.67 (m, 6H), 2.51 (br t, 4H, J=4.6 Hz).

Workup

  1. temperatureat reflux temperature for 2.5 h
  2. washwashed with 1 N NaOH (2×20 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
  4. dry with materialthe combined toluene solution and EtOAc extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by MPLC on silica gel using
  8. additiona mixture of EtOAc and hexane as eluent

Sources & evidence

ORD record
ord-75434205ec1d42b5a28aa53584300c06
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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