Trifluoroacetic acid → HCID 70624241, compound

HRID 2420165Notes

Reaction equation

HRID 2420165 reaction equation
[O:1]=[C:2]([O:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH2:31][CH2:32][CH2:33]2)[CH:3]1[O:8][CH2:7][CH2:6][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:4]1.FC(F)(F)C(O)=O.N1CCOCC1.C(=O)([O-])O.[Na+]>O>[O:1]=[C:2]([O:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH2:31][CH2:32][CH2:33]2)[CH:3]1[O:8][CH2:7][CH2:6][NH:5][CH2:4]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 70624682HCID 70624682, compound

Product 1

HCID 70624241HCID 70624241, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 g. of 2-(1-oxo-4-indanyloxymethyl)-4-triphenylmethyl morpholine was added 10 ml. of trifluoroacetic acid under ice-cooling to dissolve the morpholine and 10 ml. of water was immediately added to the solution followed by stirring for 15 minutes at 5°-10° C. Then, after neutralizing the reaction mixture with sodium hydrogencarbonate, the product was extracted with chloroform. Then, the extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The sticky residue formed was subjected to a silica gel column chromatography (column diameter 3 cm., height 7 cm,) and from the fraction recovered therefrom using a 98 : 2 mixture of chloroform and methanol as an eluting solution, 0.45 g. (yield 89.1%) of sticky 2-(1-oxo-4-indanyloxymethyl)morpholine was obtained.

Workup

  1. extractionthe product was extracted with chloroform
  2. washThen, the extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe sticky residue formed
  6. customrecovered
  7. additiona 98 : 2 mixture of chloroform and methanol as an eluting solution, 0.45 g

Sources & evidence

ORD record
ord-0866adc41828474e81b679812216228d
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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