Dimethylformamide → (+/-)-1-[(4-Chlorobenzyl)morpholin-2-yl]-2-(2-methoxyphenyl)-ethene oxalic acid salt

HRID 1532994

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][CH2:8]C[OH:10])=[CH:4][CH:3]=1.[C:13]([O:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][O:21][C:22](=O)[CH3:23])(=[O:15])C.C(N(CC)CC)C.I[C:33]1[CH:38]=[CH:37][CH:36]=C[C:34]=1[O:39][CH3:40].C(N(C(C)C)CC)(C)C.CN([CH:53]=[O:54])C>C1COCC1.CCOCC>[C:53]([OH:54])(=[O:10])[C:13]([OH:16])=[O:15].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:23][CH2:22][O:21][CH:20]([CH:19]=[CH:18][C:17]3[CH:36]=[CH:37][CH:38]=[CH:33][C:34]=3[O:39][CH3:40])[CH2:8]2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of N-(4-chlorobenzyl)-N-(2-hydroxyethyl) amine (2.00 g, 10.8 mmol) and cis-1,4-diacetoxy-2-buten (2.78 g, 16.2 mmol), triethylamine (3.26 g, 32.3 mmol), tetrakis triphenylphosphino palladium(O) (0.31 g, 0.27 mmol) in THF (20 ml) was refluxed overnight. DMF (10 ml) was added and the THF was stripped off in vacuum. Addition of 2-iodoanisole (3.8 g, 16.2 mmol) and diisopropylethylamine (2.8 g, 21.6 mmol) was followed by heating to 130° C. overnight. Ether was added and the organics were washed twice with aqueous sodium hydroxide (1 M). Chromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base. Dissolution in ether and precipitation with oxalic acid gave the title compound. Yield 1.0 g, 21%. mp 178-180° C.

Workup

temperaturewas refluxed overnight
washthe organics were washed twice with aqueous sodium hydroxide (1 M)
customChromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base
customprecipitation with oxalic acid

Sources & evidence

ORD record: ord-5f20e29e5b034c86b77ca0e8bd73a0a0
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207662B1

Linked notes

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