Morpholine → HCID 67171234, compound

HRID 1506466Notes

Reaction equation

HRID 1506466 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][CH2:8][N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:7][CH2:8][N:9]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 57366378Tert-butyl 7-bromo-4-oxo-3,4-dihydroquinoline-1(2h)-carboxylate

Product 1

HCID 67171234HCID 67171234, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of tert-butyl 7-bromo-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (0.500 g, 1.53 mmol) and morpholine (0.668 mL, 7.66 mmol) in toluene (10 mL) at 0° C. was added titanium(IV) chloride [1M in toluene] (0.843 mL, 0.843 mmol) dropwise. The ice-bath was removed, and the orange, heterogeneous reaction mixture was stirred at room temperature overnight. The heterogeneous, orange reaction mixture was filtered under reduced pressure through a pad of Celite which was then rinsed with toluene (3×10 mL). The pale yellow filtrate was concentrated under reduced pressure to give tert-butyl 7-bromo-4-morpholinoquinoline-1(2H)-carboxylate (0.598 g, 1.513 mmol, 99% yield) as a yellow oil. The product had LC/MS M+1=395.1 and 397.1.

Workup

  1. customThe ice-bath was removed
  2. filtrationThe heterogeneous, orange reaction mixture was filtered under reduced pressure through a pad of Celite which
  3. washwas then rinsed with toluene (3×10 mL)
  4. concentrationThe pale yellow filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb38b9b2899f4014b7330e2780decbee
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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