p-Toluenesulfonic acid → HCID 12800267, compound

HRID 2420178Notes

Reaction equation

HRID 2420178 reaction equation
O[C:2]([O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH2:23][CH2:22]2)([CH:9]1[O:14][CH2:13][CH2:12][N:11]([CH:15]([CH3:17])[CH3:16])[CH2:10]1)C1C=CC=CC=1.[C:28]1(C)[CH:33]=[CH:32][C:31](S(O)(=O)=O)=[CH:30][CH:29]=1>C1(C)C(C)=CC=CC=1>[CH:15]([N:11]1[CH2:12][CH2:13][O:14][CH:9]([CH2:2][O:18][C:19]2[CH:20]=[C:21]3[C:25]([C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH2:22]3)=[CH:26][CH:27]=2)[CH2:10]1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20313245HCID 20313245, compound

Product 1

HCID 12800267HCID 12800267, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 50 ml. of xylene was dissolved 1.5 g. of 2-(1-hydroxy-1-phenyl-5-indanyloxymethyl)-4-isopropylmorpholine and after adding to the solution 5 mg. of p-toluenesulfonic acid, the mixture was refluxed for 8 hours. Thereafter, xylene was distilled off under reduced pressure and the residue was adsorbed on a silica gel column prepared from 100 ml. of silica gel in chloroform and eluted using ethyl acetate as the eluent. 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 dried to provide 1.0 g. (yield 70.2%) of 4isopropyl-2-(3-phenyl-6-indenyloxymethyl)morpholine. The citrate of the product had a melting point of 107°-109° C.

Workup

  1. distillationThereafter, xylene was distilled off under reduced pressure
  2. customprepared from 100 ml
  3. washof silica gel in chloroform and eluted
  4. customAfter removing the first 10 ml
  5. customof the subsequent ethyl acetate eluate was collected
  6. customdried
  7. customto provide 1.0 g

Sources & evidence

ORD record
ord-cddb2dd860b74a67858b3ddac2dce583
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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