Morpholine → 4-(2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5-yl)morpholine

HRID 1506412Notes

Reaction equation

HRID 1506412 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][CH:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:13](=O)[CH2:12][CH2:11][CH2:10][C:9]=3[N:8]=2)[CH2:4][O:3]1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:18])[O:6][CH:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:13]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:12][CH2:11][CH2:10][C:9]=3[N:8]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 671722122-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5(6H)-one

Product 1

HCID 671700704-(2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5-yl)morpholineYield 83.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5(6H)-one (0.182 g, 0.736 mmol) and morpholine (0.321 mL, 3.68 mmol) in toluene (3 mL) at 0° C. was added titanium(IV) chloride (1.0 M in toluene) (0.405 mL, 0.405 mmol) dropwise. The ice-bath was removed, and the orange, heterogeneous reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered 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 4-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroquinolin-5-yl)morpholine (0.194 g, 0.613 mmol, 83% yield) as a yellow oil.

Workup

  1. customThe ice-bath was removed
  2. filtrationThe reaction mixture was filtered 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-928f7089798c477fbb6d016513d01a89
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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