o-Phenetidine → 4-Benzyl-2-(2-ethoxyanilino)methylmorpholine toluene-p-sulphonate

HRID 437181

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]=1

Participants

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-d7512c75706848f79c8959a5584299b7
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04029786

Linked notes

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