Morpholine → 4-[6-Chloro 4-(3-chloro-4-fluoro-phenyl)-pyridin-2-yl]-morpholine

HRID 230946Notes

Reaction equation

HRID 230946 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 866103112,3-Dichloro-4-(3-chloro-4-fluoro-phenyl)-pyridine

Product 1

HCID 577611414-[6-Chloro 4-(3-chloro-4-fluoro-phenyl)-pyridin-2-yl]-morpholine

Procedure

Stir the solution of 2,3-dichloro-4-(3-chloro-4-fluoro-phenyl)-pyridine (100 mg) in morpholine (2 mL) 3 hours at 80° C., concentrate, partition between H2O and EtOAc, dry over Na2SO4, and concentrate under vacuum. Purify by preparative TLC (3:1 hexanes/EtOAc) to give 4-[6-chloro-4-(3-chloro-4-fluoro-phenyl)-pyridin-2-yl]-morpholine.

Workup

  1. concentrationconcentrate
  2. custompartition between H2O and EtOAc
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate under vacuum
  5. customPurify by preparative TLC (3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-d7489e9033b24ce3b102dbdd67f5af71
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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