o-Phenetidine → 4-Benzyl-2-(2-ethoxyanilino)methylmorpholine toluene-p-sulphonate
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:18]1[CH2:23][CH2:22][O:21][CH:20]([CH2:24][O:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOCC>[C:32]1([CH3:35])[CH:31]=[CH:30][C:29]([S:26]([OH:28])(=[O:25])=[O:27])=[CH:34][CH:33]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([CH2:24][NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[O:3][CH2:1][CH3:2])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 2-ethoxyaniline (14.0 g.) and 4-benzyl-2-toluene-p-sulphonyloxymethylmorpholine (18.6 g.) is stirred and heated on the steam bath (95°C.) under nitrogen for 24 hours. The mixture is cooled and ether added. The solid thus obtained is collected and crystallised from ethyl acetate to give 4-benzyl-2-(2-ethoxyanilino)methylmorpholine toluene-p-sulphonate, m.p. 127°C. The toluene sulphonate salt is converted into the corresponding dihydrochloride by basifying it with dilute sodium hydroxide solution, extracting the base into ether (3 × 200 ml.), washing the ethereal extract with water and then drying it over anhydrous magnesium sulphate followed by filtration and treatment of the ethereal solution of base with ethereal hydrochloric acid solution. The 4-benzyl-2-(2-ethoxyanilino)methylmorpholine dihydrochloride melts at 226°C. after crystallisation from methanol/ethyl acetate.
Workup
- temperatureThe mixture is cooled
- customThe solid thus obtained
- customis collected
- customcrystallised from ethyl acetate
Sources & evidence
- ORD record
- ord-aa2bd4fd26c64a518a34e58eba5a78c1
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03974158
Reaction notes
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