o-Phenetidine → 2-(2-Ethoxyanilino)methyl-4-propylmorpholine toluene-p-sulphonate

HRID 1283101Notes

Reaction equation

HRID 1283101 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])[CH3:2].[CH2:11]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH2:20][O:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:15]1)[CH2:12][CH3:13]>C1(C)C(C)=CC=CC=1>[C:28]1([CH3:31])[CH:27]=[CH:26][C:25]([S:22]([OH:24])(=[O:21])=[O:23])=[CH:30][CH:29]=1.[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH2:20][CH:16]1[O:17][CH2:18][CH2:19][N:14]([CH2:11][CH2:12][CH3:13])[CH2:15]1)[CH3:2]

Participants

4

Reactant 2

HCID 7203o-PhenetidineHCID 214303624-n-Propyl-2-toluene-p-sulphonyloxymethylmorpholine

Product 1

HCID 215192902-(2-Ethoxyanilino)methyl-4-propylmorpholine toluene-p-sulphonate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 2-ethoxyaniline (4.8 g.) and 4-n-propyl-2-toluene-p-sulphonyloxymethylmorpholine (10 g.) in xylene (50 ml.) is heated under reflux in an atmosphere of nitrogen for 60 hours. A resinous solid separates from the solvent which is distilled under reduced pressure. The residual sticky solid is washed with ether to give a yellow solid which is crystallised from methanol/ether to give 2-(2-ethoxyanilino)methyl-4-propylmorpholine toluene-p-sulphonate, m.p. 169°-172°C.

Workup

  1. temperatureunder reflux in an atmosphere of nitrogen for 60 hours
  2. distillationA resinous solid separates from the solvent which is distilled under reduced pressure
  3. washThe residual sticky solid is washed with ether
  4. customto give a yellow solid which
  5. customis crystallised from methanol/ether

Sources & evidence

ORD record
ord-aba26f2c82b34e1e9d68b35ada05950b
Source dataset
uspto-grants-1976_08
Patent number
US03974158

Reaction notes

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