3-Methoxyaniline → HCID 21519218, compound

HRID 1283000Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[CH2:10]([N:17]1[CH2:22][CH2:21][O:20][CH:19]([CH2:23][O:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCOCC>[C:31]1([CH3:34])[CH:30]=[CH:29][C:28]([S:25]([OH:27])(=[O:24])=[O:26])=[CH:33][CH:32]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][O:20][CH:19]([CH2:23][NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 3-methoxyaniline (12.5 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-(3-methoxyanilino)methylmorpholine toluene-p-sulphonate, m.p. 102-103°C. The toluene-p-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-(3-methoxyanilino)methylmorpholine dihydrochloride monohydrate melts at 116-118°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-7d1da896756e4d32bde7f12d0bf50ea1
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03974156

Reaction notes

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