Methylamine → HCID 66781646, compound

HRID 1360149Notes

Reaction equation

HRID 1360149 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:16])[NH:14][C:13](=O)[CH2:12][O:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:17][NH2:18]>O1CCCC1.C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH3:16])[CH2:10][O:11][CH2:12][C:13]([CH2:17][NH2:18])=[N:14]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 66781699HCID 66781699, compound

Product 1

HCID 66781646HCID 66781646, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 69.5 mmol of 5-(4-methoxyphenyl)-5-methylmorpholin-3-one in 200 ml of tetrahydrofuran and 25 ml of benzene is cooled to 0° C. and saturated with methylamine. A solution of 19 g of titanium tetrachloride in 25 ml of benzene is added dropwise over the course of 15 minutes. After addition is complete, the reaction mixture is heated to reflux for 3 hours. The reaction mixture is then cooled to 0° C. and cautiously quenched with 60 ml of water. It is filtered through Hyflo, and the filter cake is washed several times with tetrahydro-furan. The phases of the filtrate are separated, and the organic phase is dried with sodium sulphate and evaporated. The title compound is identified from the residue oh the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux for 3 hours
  4. customcautiously quenched with 60 ml of water
  5. filtrationIt is filtered through Hyflo
  6. washthe filter cake is washed several times with tetrahydro-furan
  7. customThe phases of the filtrate are separated
  8. dry with materialthe organic phase is dried with sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-e7fe7931408940f58530424d46bc4ab2
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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