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

HRID 1532994

反応式

HRID 1532994 の反応式
[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

参加物

9

反応物 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 68257o-IodoanisoleHCID 81531DiisopropylethylamineHCID 4244522-(4-Chloro-benzylamino)-ethanolHCID 643799(2Z)-but-2-ene-1,4-diyl diacetate

生成物 1

HCID 69687101(+/-)-1-[(4-Chlorobenzyl)morpholin-2-yl]-2-(2-methoxyphenyl)-ethene oxalic acid salt

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
130 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5f20e29e5b034c86b77ca0e8bd73a0a0
出典データセット
uspto-grants-2001_03
特許番号
US06207662B1

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