p-Toluenesulfonic acid monohydrate → 2-{[(3-Methyl-1H-inden-7-yl)oxy]methyl}morpholine

HRID 2420167Notes

Reaction equation

HRID 2420167 reaction equation
O[C:2]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][CH2:15]2)([CH:4]1[O:9][CH2:8][CH2:7][NH:6][CH2:5]1)C.O.[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:21][C:15]1[C:16]2[C:12](=[C:11]([O:10][CH2:2][CH:4]3[O:9][CH2:8][CH2:7][NH:6][CH2:5]3)[CH:19]=[CH:18][CH:17]=2)[CH2:13][CH:14]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20313237HCID 20313237, compound

Product 1

HCID 128002622-{[(3-Methyl-1H-inden-7-yl)oxy]methyl}morpholineYield 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 20 ml. of anhydrous toluene was dissolved 100 mg. of 2-(1-hydroxy-1-methyl-4-indanyloxymethyl)morpholine and after adding thereto 10 mg. of p-toluenesulfonic acid monohydrate, the mixture was refluxed for 4 hours. After cooling, the reaction mixture was washed successively with aqueous 3% sodium hydrogencarbonate solution and water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue formed was subjected to a silica gel column chromatography (diameter 1.5 cm., height 7 cm.) and from the fraction recovered therefrom using a 98 : 2 mixture of chloroform and methanol as an eluting solution, 69 mg. (yield 74.5%) of sticky 2-(3-methyl-7-indenyloxymethyl)morpholine was obtained. The oxalate of the product had a melting point of 151°-152° C.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed successively with aqueous 3% sodium hydrogencarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue formed
  6. customrecovered
  7. additiona 98 : 2 mixture of chloroform and methanol as an eluting solution, 69 mg

Sources & evidence

ORD record
ord-dc6c23128e4e4478b334b987bf954b50
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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