Morpholine → 5-(4-Morpholinylmethyl)-8-quinolinol

HRID 23939Notes

Reaction equation

HRID 23939 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2>C(Cl)(Cl)Cl>[O:4]1[CH2:5][CH2:6][N:1]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 4168815-(Chloromethyl)quinolin-8-ol

Product 1

HCID 10903035-(4-Morpholinylmethyl)-8-quinolinolYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Morpholine (1.9 ml; 21.8 mmol) was added to a solution of 5-chloromethyl-8-hydroxyquinoline (1.98 g; 8.34 mmol) in CHCl3 (50 ml) at 5° C. The reaction mixture was stirred overnight at room temperature. Then CHCl3 (100 ml) was added and the solution was washed with 5% NaHCO3 (2×50 ml), followed by brine (50 ml), and dried over Na2SO4. The solution was filtered and evaporated under vacuum to dryness. The residue was crystallized from hexane-CHCl3 and gave 1.2 g (59%) of the title product. M.p. 130° C. TLC (CHCl3; MeOH; NH3=8:2:0.5. Rf=0.69.

Workup

  1. washthe solution was washed with 5% NaHCO3 (2×50 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationThe solution was filtered
  4. customevaporated under vacuum to dryness
  5. customThe residue was crystallized from hexane-CHCl3

Sources & evidence

ORD record
ord-d327b4f511f44069aecb5e4b9549be84
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Reaction notes

Loading…