p-Toluenesulfonic acid → HCID 12800269, compound

HRID 2420181Notes

Reaction equation

HRID 2420181 reaction equation
O[C:2]([O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][CH2:18][CH2:17]2)([CH:4]1[O:9][CH2:8][CH2:7][N:6]([CH:10]([CH3:12])[CH3:11])[CH2:5]1)C.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH:10]([N:6]1[CH2:7][CH2:8][O:9][CH:4]([CH2:2][O:13][C:14]2[CH:15]=[C:16]3[C:20]([C:19]([CH3:23])=[CH:18][CH2:17]3)=[CH:21][CH:22]=2)[CH2:5]1)([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20313229HCID 20313229, compound

Product 1

HCID 12800269HCID 12800269, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3.05 g. of oily 2-(1-hydroxy-1-methyl-5-indanyloxymethyl)-4-isopropylmorpholine, 100 ml. of xylene, and 20 mg. of p-toluenesulfonic acid was refluxed with stirring for 4 hours and then the solvent was distilled off. Then, the residue formed was adsorbed on a silica gel column prepared from 100 ml. of silica gel in chloroform and eluted with ethyl acetate. After removing the first 10 ml. of the ethyl acetate eluate emerging from the column, 200 ml. of the subsequent ethyl acetate eluate was collected and concentrated under reduced pressure to provide 2.1 g. (yield 73.3%) of 4-isopropyl-2-(3-methyl-6-indenyloxymethyl)morpholine. The citrate of the product had a melting point of 159°-161° C.

Workup

  1. additionA mixture of 3.05 g
  2. distillationthe solvent was distilled off
  3. customThen, the residue formed
  4. customprepared from 100 ml
  5. washof silica gel in chloroform and eluted with ethyl acetate
  6. customAfter removing the first 10 ml
  7. customof the subsequent ethyl acetate eluate was collected
  8. concentrationconcentrated under reduced pressure
  9. customto provide 2.1 g

Sources & evidence

ORD record
ord-b5dfc1a5f6974098bde1f919086db1eb
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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