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4-Fluoro-N-methylaniline → N'-{[4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-N-(4-fluorophenyl)-N-methylurea

HRID 1371440
Notes
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Reaction equation

HRID 1371440 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH:17]([CH2:21][NH:22][C:23](=[O:34])OC2C=CC([N+]([O-])=O)=CC=2)[CH2:16]1>N1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH:17]([CH2:21][NH:22][C:23](=[O:34])[N:6]([C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[CH3:7])[CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 680244-Fluoro-N-methylanilineHCID 115394484-Nitrophenyl [4-(3,4-dichlorobenzyl)morpholin-2-yl]methylcarbamate

Product 1

HCID 17984716N'-{[4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-N-(4-fluorophenyl)-N-methylurea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

4-Fluoro-N-methylaniline (0.007 ml) was added to a solution of Intermediate 10 (0.025 g) in anhydrous pyridine (1 ml). The mixture was heated at 110° C. in a thick walled glass vial (Reactivial) for 20 h. The mixture was evaporated to remove the pyridine, and partitioned between ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate solution (10 ml). The organic layer was washed with further sodium bicarbonate (10 ml×5), brine (10 ml), dried (MgSO4), concentrated in vacuo. The residue was purified by chromatography on silica gel (Trikonex flash tube 2002, 2 g), eluting with 70% ethyl acetate in cyclohexane to give the title compound as a pale yellow gum 0.014 g. LCMS (system A) Rt 2.52 min, Mass Spectrum m/z 426 [MH+].

Workup

  1. customThe mixture was evaporated
  2. customto remove the pyridine
  3. custompartitioned between ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate solution (10 ml)
  4. washThe organic layer was washed with further sodium bicarbonate (10 ml×5), brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (Trikonex flash tube 2002, 2 g)
  8. washeluting with 70% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-9eaf946f940643b391f5660be3be364b
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07157457B2

Reaction notes

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