4,4'-Dimethoxybenzophenone → HCID 86662309, compound

HRID 1894925Notes

Reaction equation

HRID 1894925 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([CH2:17][NH2:18])=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][O:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=O)=[CH:23][CH:22]=1.C1COCC1.C(N(CC)CC)C>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl.O>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]([C:24]2[CH:35]=[CH:36][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[N:18][CH2:17][C:11]2[CH:10]=[C:9]3[C:14]([CH:15]=[CH:16][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:8]3)=[CH:13][CH:12]=2)=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 70324,4'-DimethoxybenzophenoneHCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 66740064HCID 66740064, compound

Product 1

HCID 86662309HCID 86662309, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

C-(2-Phenylquinolin-7-yl)methylamine (170 mg, 0.73 mmol) and 4,4′-dimethoxybenzophenone (176 mg, 0.73 mmol) were added to a flask under nitrogen. THF (4 mL) and triethylamine (0.30 mL, 2.2 mmol) were then added. The mixture was cooled to −78° C. and titanium tetrachloride (0.080 mL, 0.73 mmol) was added. The reaction mixture was allowed to warm to room temperature. After stirring for 30 minutes the mixture was cooled to −78° C. and triethylamine (2 mL) was added followed by water (3 mL). The mixture was warmed to room temperature and DCM was added. The organic solution was washed with water, dried over sodium sulfate, filtered, and concentrated to dryness in vacuo. The resultant yellow oil was purified by silica gel chromatography (eluted with DCM/heptane 2:1). A light yellow solid (0.247 g, yield 74%) was obtained.

Workup

  1. temperatureto warm to room temperature
  2. temperaturewas cooled to −78° C.
  3. temperatureThe mixture was warmed to room temperature
  4. washThe organic solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo
  8. customThe resultant yellow oil was purified by silica gel chromatography (eluted with DCM/heptane 2:1)

Sources & evidence

ORD record
ord-c9250d2d1c8e4ad194df8f428e8481a0
Source dataset
uspto-grants-2013_08
Patent number
US08513415B2

Reaction notes

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